HCID 86723604, compound → (2S,4S)-1-(Tert-butoxycarbonyl)-4-ethylpyrrolidine-2-carboxylic acid

HRID 590668Notes

Reaction equation

HRID 590668 reaction equation
[CH2:1]([C@@H:3]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:5]([C:15]([O:17]CC2C=CC=CC=2)=[O:16])[CH2:4]1)[CH3:2]>CO.[Pd]>[C:11]([O:10][C:8]([N:6]1[CH2:7][C@@H:3]([CH2:1][CH3:2])[CH2:4][C@H:5]1[C:15]([OH:17])=[O:16])=[O:9])([CH3:12])([CH3:13])[CH3:14]

Participants

4

Reactant 1

HCID 86723604HCID 86723604, compound

Product 1

HCID 67085685(2S,4S)-1-(Tert-butoxycarbonyl)-4-ethylpyrrolidine-2-carboxylic acidYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2S,4S)-2-benzyl 1-tert-butyl 4-ethylpyrrolidine-1,2-dicarboxylate (18 g, 54.1 mmol), Pd/C (3.6 g) in MeOH (1 L) was hydrogenated at room temperature overnight. TLC showed that the reaction was completed. The mixture was filtered by Celite. The filtrate was concentrated to afford (2S,4S)-1-(tert-butoxycarbonyl)-4-ethylpyrrolidine-2-carboxylic acid (10 g, 77%) as white solid. 1H NMR: 400 MHz CDCl3: δ 9.88 (br, 1H), 4.31-4.19 (m, 1H), 3.82-3.68 (m, 1H), 3.03-2.95 (m, 1H), 2.49-2.39 (m, 1H), 2.12-2.03 (m, 1H), 1.81-1.56 (m, 1H), 1.45 (d, J=8 Hz, 11H), 0.92 (t, J=6 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered by Celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d02458d6a3624ab88be3be13cd189ff5
Source dataset
uspto-grants-2016_01
Patent number
US09233974B2

Reaction notes

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