(S)-3-benzyloxycarbonylamino-3-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester → tert-butyl (S)-3-amino-3-methylpyrrolidine-1-carboxylate

HRID 519153Notes

Reaction equation

HRID 519153 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@:10]([NH:14]C(OCC2C=CC=CC=2)=O)([CH3:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@:10]([NH2:14])([CH3:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86727546(S)-3-benzyloxycarbonylamino-3-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86328910tert-butyl (S)-3-amino-3-methylpyrrolidine-1-carboxylateYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (S)-3-benzyloxycarbonylamino-3-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (enantiomer 1, SFC (Table 1, Method 51) Rt=3.693 min, 1.7 g, 5.08 mmol) and Pd/C (10%, 0.2 g, 0.19 mmol) in MeOH (10 mL) was stirred at ambient temperature under an atmosphere of H2 (1 atm) for 2 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give (S)-3-amino-3-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.12 g, 67%). 1H NMR (400 MHz, CDCl3) δ 3.62-3.06 (m, 4H), 1.88-1.70 (m, 2H), 1.48 (s, 9H), 1.34-1.26 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1e423b16d090478eb56ba4b0b3298257
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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