(S)-methyl 2-(benzyloxycarbonylamino)-3-(1H-indol-5-yl)propanoate → Methyl (S)-2-Amino-3-(5-indolyl)propanoate

HRID 58854Notes

Reaction equation

HRID 58854 reaction equation
C(OC([NH:11][C@@H:12]([CH2:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[CH:21]2)[C:13]([O:15][CH3:16])=[O:14])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][C@@H:12]([CH2:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[CH:21]2)[C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 1

HCID 117608073(S)-methyl 2-(benzyloxycarbonylamino)-3-(1H-indol-5-yl)propanoate

Product 1

HCID 117608083Methyl (S)-2-Amino-3-(5-indolyl)propanoateYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-methyl 2-(benzyloxycarbonylamino)-3-(1H-indol-5-yl)propanoate (3.27 g, 9.39 mmol) in methanol (30 mL) was added Pd/C (10%, 200 mg). The mixture was stirred under hydrogen atmosphere at ambient temperature for 1 h and then filtered through a pad of Celite. The filtrate was concentrated to afford (S)-methyl 2-amino-3-(1H-indol-5-yl)propanoate (1.8 g, 88% yield) as a light green solid, which was used directly without further purification.

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-183e550206e54803bd81539c4ffe7cbe
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

Loading…