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Experimental Procedures

This section provides procedures and protocols to perform reactions

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Process Chemistry

Components of process chemistry is explained in detail here

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General Organic Synthesis

It is all about synthesis, mechanism, reagents, references etc.

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Alcohol to other Functional Groups
Aldehyde/Ketone to other Functional Groups

Carboxylic acid to other Functional Groups

Ester to other Functional Groups

Nitrile to other Functional Groups

Using Acidic condition

Using DIBAL-H

Borane.THF (BH3.THF) reduction

Borane.Me2S (BH3.Me2S) or BMS reduction

Pd/C reduction

Raney Ni reduction

Using Urea-Hydrogen peroxide (UHP)

Pinner reaction (HCl, alcohol)

Amide to other Functional Groups

Hofmann rearrangement (for 1o amide only)

Using POCl3

Using SOCl2

Using T3P

Using TFAA

Using Cyanuric chloride

Amide hydrolysis under acidic condition

Aromatic Substitution reactions (SNAr)

Topic name

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Haloalkane to other Functional Groups

Using CH3COSH, K2CO3

(a) Phalimide reaction (b) Phthalimide cleavage (2 steps)

(a) NaN3 (d) Reduction (Pd/C)

Using NaCN or KCN

Using Triethylphosphite, NaOH

(a) NaNO2 (b) HCl

Alkene to other Functional Groups

(a) Ozonolysis (b) Reduction by NaBH4 (2 steps)

(a) Hydroboration (b) Oxidation (2 steps)

Using OsO4, NaIO4

Using K2OsO4, NaIO4

Using Pd/C, H2

Using Pd/C, HCOONH4

Using PtO2, H2

Using Zn, NH4Cl (specific cases)

Using Raney Ni, NaBH4

Using NaBH(OAc)3 (specific cases)

Using LiAlH4 (specific cases)

Asymmetric Reductions

(a) Bromination (b) Elimination (2 steps)

Using OsO4, NMO

Using K2OsO4, NMO

Using mCPBA

Alkyne to other Functional Groups

Using Pd/C, H2

Using Lindlar Catalyst

Using Br2

Aromatic Electrophilic reactions

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Amine to other Functional Groups

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Epoxide to other Functional Groups

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Ether to other Functional Groups

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Aliphatic Substitution reactions (SN1 and SN2)

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Alkane to other Functional Groups

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Elimination reactions (E1 and E2)

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Acid chloride/Acid anhydride to other Functional Groups

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——– to other Functional Groups

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Alcohol
Protecting GroupProtection ConditionDeprotection condition
1. TMSCl, Py, DCM

2. TMSOTf, Et3N (or) 2.6-Lutidine, DCM		1. HCl, THF, H2O


1. TBDMSCl, Im, DCM (or) DMF

2. TBDMSOTf, 2,6-Lutidine, DCM



1. HCl, THF (or) MeOH, H2O

2. PPTS or CSA, EtOH (or) MeOH

3. BF3.OEt2, DCM

4. TBAF, THF

1. TIPSCl, DMAP, DMF


1. HCl, THF (or) MeOH, H2O

2. TBAF, THF
1. TBDPSCl, Im (or) DMAP, DMF (or) THF (or) DCM
1. TBAF, THF
1. BnBr, K2CO3, acetone

2. BnBr, NaH, TBAI, THF		1. Pd/C, H2, EtOH (or) MeOH (or) EtOAc

2. Pd(OH)2/C, H2, EtOH (or) MeOH
1. PMBCl, NaH, THf (or) DMF

2. PMB trichloroacetamidate, TfOH (cat.), DCM		1. DDQ, buffer (pH 7), DCM
1. Ac2O, DMAP, DCM (or) toluene

2. Ac2O, Py (solvent)

1. LiOH, THF, H2O

2. KOH. MeOH, H2O

3. K2CO3, MeOH
1. BzCl, DMAP (or) Py, DCM

2. BzCl, Py (solvent)		1. KOH. EtOH

2. K2CO3, MeOH, THF
1. MOMCl, DMAP (or) DIPEA, DCM

1. HCl, MeOH, H2O

2. TMSBr, DCM
1. MEMCl, DIPEA, DCM1. ZnBr2, DCM
1. 3,4-Dihydropyran (DHP), PTSA (or) PPTS (cat.), DCM1.. PTSA (or) PPTS, MeOH (or) EtOH

2. AcOH, H2O
1. NaH, MeI, THF1. TMSCl, NaI, CH3CN, H2O

2. TMSI, CH3CN

1,2-Diol
Protecting GroupProtection ConditionDeprotection condition
1. 2,2-Dimethoxypropane, PPTS, DMF

2. 2,2-Dimethoxypropanev, CSA, DCM

3. CuSO4, acetone		1. HCl, THF (or) MeOH, H2O

2. TFA, CH3CN, H2O


1. PhCH(OMe)2, PPTS, Toluene1. Pd(OH)2/C, H2, EtOH
1. CDI, toluene

2. CDI, NaH, THF (or) DMF
1. KOH, MeOH
Amine
Protecting GroupProtection ConditionDeprotection condition
1. Boc2O, Et3N, DCM

2. Boc2O, NaHCO3, EtOAc, H2O
1. TFA, DCM

2. AcCl, EtOH

3. TMSOTf, Et3N, DCM
1. BnCOOCl (CbzCl), Na2CO3, THF

2. BnCOOCl (CbzCl), K2CO3, CH3CN		1. Pd/C (or) Pd(OH)2,, H2, MeOH

2. Pd/C, HCOONH4, MeOH
1. BnBr, K2CO3, MeOH1. Pd/C, H2, HCl, EtOH
1. Ac2O, DMAP, DCM

2. Ac2O, Py (solvent)		1. HCl, MeOH

2. KOH, MeOH, H2O
1. TFAA, Py, DCM1. K2CO3, MeOH, H2O

2. NaOMe, MeOH, DCM
1. ClCOOMe, DMAP, DCM1. HBr, AcOH
1. HCOOEt, Et3N

2. HCOOAc, HCOOH		1. HCl, MeOH, H2O

2. NaOH, MeOH
Aldehyde,
Ketone
Protecting GroupProtection ConditionDeprotection condition
1. CH(OMe)3, PTSA, MeOH1. PPTS, acetone, H2O

1. CH(OEt)3, PTSA, EtOH		1. HCl, THF, H2O
1. (CH2OH)2, PTSA (or) Dowex acidic resin, toluene
1. HCl, MeOH, H2O

2. PTSA (or) PPTS, acetoe, H2O
Carboxylic
acid
Protecting GroupProtection ConditionDeprotection condition
1. BnOH, PTSA, toluene1. Pd/C, H2, MeOH (or) EtOAc
1. Fischer Esterification
(cat. H+, MeOH)		1. LiOH (or) NaOH, THF (or) MeOH, H2O
Phenol
Protecting GroupProtection ConditionDeprotection condition
1. TBDMSCl, Im, DMF1. HCl, THF (or) CH3CN, H2O

1. TIPSCl, Im, DMF		1. TBAF, THF
1. BnBr, K2CO3, CH3CN (or) DMF

2. BnBr, AgO, DCM		1. Pd/C, H2, MeOH

2. HBr, DCM
1. Me2SO4, KOH, MeOH, H2O

2. Me2SO4, K2CO3, acetone

3. MeI, NaOH, TBAB, H2O

4. Me3O+BF4–, proton sponge, DCM
[proton sponge is 1,8-Bis(dimethylamino)naphthalene]		1. BBr3, DCM

2. Pyr.HCl

3. NaSEt, DMF
PG strategies

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