(+/-)-3-(5-methoxy-1H-indol-3-yl)-2-methyl-2-nitro-propionic acid methyl ester → (RS)-2-amino-3-(5-methoxy-1H-indol-3-yl)-2-methyl-propionic acid methyl ester

HRID 41054Notes

Reaction equation

HRID 41054 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]([CH3:20])([N+:17]([O-])=O)[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][CH:7]=1>CO>[CH3:1][O:2][C:3](=[O:21])[C:4]([NH2:17])([CH3:20])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][CH:7]=1

Participants

3

Reactant 1

HCID 58212093(+/-)-3-(5-methoxy-1H-indol-3-yl)-2-methyl-2-nitro-propionic acid methyl ester

Product 1

HCID 58212094(RS)-2-amino-3-(5-methoxy-1H-indol-3-yl)-2-methyl-propionic acid methyl esterYield 90.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (+/−)-3-(5-methoxy-1H-indol-3-yl)-2-methyl-2-nitro-propionic acid methyl ester (4.26 g) in methanol (80 mL) wet Raney nickel (ca 12 g) is added, and the mixture is stirred under hydrogen at atmospheric pressure at room temperature overnight. The solid is filtered through Celite, is washed with methanol, and the filtrate is concentrated. Column chromatography of the residue (dichloromethane-methanol, 98:2→95:5) gives the title compound (3.45 g, 90%). M.p. 131-132° C. (from ethyl acetate-light petroleum).

Workup

  1. filtrationThe solid is filtered through Celite
  2. washis washed with methanol
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-dd3861a188284abbbc62a2312e38df54
Source dataset
uspto-grants-2013_09
Patent number
US08530493B2

Reaction notes

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