phenylmethyl (2S)-2-(aminocarbonyl)-3,3-dimethyl-1-pyrrolidinecarboxylate → (S)-3,3-dimethylpyrrolidine-2-carboxamide

HRID 1014156Notes

Reaction equation

HRID 1014156 reaction equation
[NH2:1][C:2]([C@@H:4]1[C:8]([CH3:10])([CH3:9])[CH2:7][CH2:6][N:5]1C(OCC1C=CC=CC=1)=O)=[O:3]>CO.[Pd]>[CH3:9][C:8]1([CH3:10])[CH2:7][CH2:6][NH:5][C@@H:4]1[C:2]([NH2:1])=[O:3]

Participants

4

Reactant 1

HCID 57878111phenylmethyl (2S)-2-(aminocarbonyl)-3,3-dimethyl-1-pyrrolidinecarboxylate

Product 1

HCID 54083353(S)-3,3-dimethylpyrrolidine-2-carboxamideYield 102.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a 200 ml flask was dissolved phenylmethyl (2S)-2-(aminocarbonyl)-3,3-dimethyl-1-pyrrolidinecarboxylate (0.0192 mol, 5.3 g) in 80 ml methanol at 20° C. 10% Pd/C (Degussa type, 0.53 g) was added and the mixture was stirred for 5 hr under atmospheric H2. The catalyst was filtered and the reaction was concentrated yielding 2.8 g (quantitative) of 3,3-dimethyl-L-prolinamide as a white solid. LCMS (ESI+)=143 m/z (MH+). 1H NMR (400 MHz, CDCl3)— rotomers δ 7.20 (bs, 1H), 6.20 (bs, 1H), 3.32 (s, 1H), 3.05-3.01 (m, 2H), 2.50 (bs, 1H), 1.67-1.62 (m, 2H), 1.23 (s, 3H), 0.97 (s, 3H). [α]D +1.2° (c=0.5, methanol)

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-f92d4124427b4fd1bc0dad2907108bc6
Source dataset
uspto-grants-2011_07
Patent number
US07982053B2

Reaction notes

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