(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester → 1-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate

HRID 1504334Notes

Reaction equation

HRID 1504334 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1>C(Cl)Cl>[O:1]=[C:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1

Participants

3

Reactant 1

HCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Product 1

HCID 109884851-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (40 g, 157 mmol) in DCM (500 mL) was added DMP (80 g, 189 mmol) at 0° C. and the reaction mixture was stirred at RT for 4 h, quenched with NaHSO3, extracted with DCM and washed with NaHCO3. The organic phase was concentrated to provide the title intermediate (33 g, 89% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ(ppm) 1.51 (s, 9H), 2.550-2.597 (d, 1H, J=18.8 Hz), 2.876-2.944 (t, 1H, J=13.6 Hz), 3.895 (s, 3H), 3.766-3.895 (m, 1H), 4.696-4.814 (m, 1H).

Workup

  1. customquenched with NaHSO3
  2. extractionextracted with DCM
  3. washwashed with NaHCO3
  4. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-38d1496a6e6c405d84639f8db61809bb
Source dataset
uspto-grants-2015_12
Patent number
US09212168B2

Reaction notes

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