Benzyl succinimido carbonate → (3aR,6aR)-Hexahydro-pyrrolo[3,4-b]pyrrole-1,5-dicarboxylic acid 5-benzyl ester 1-tert-butyl ester

HRID 1027867Notes

Reaction equation

HRID 1027867 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]2[CH2:13][NH:14][CH2:15][C@H:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([O:23][C:24](ON1C(=O)CCC1=O)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]2[CH2:13][N:14]([C:24]([O:23][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:25])[CH2:15][C@H:9]12)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 29949076rac-tert-butyl (3aR,6aR)-octahydropyrrolo(2,3-c)pyrrole-1-carboxylate

Product 1

HCID 44221919(3aR,6aR)-Hexahydro-pyrrolo[3,4-b]pyrrole-1,5-dicarboxylic acid 5-benzyl ester 1-tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3aR,6aR)-Hexahydro-pyrrolo[3,4-b]pyrrole-1-carboxylic acid tert-butyl ester (CAS #370880-09-4) (3.0 g, 12.5 mmol) and N-(benzyloxycarbonyloxy)-succinimide (3.42 g, 13.7 mmol) were mixed in 15 ml of dichloromethane. The mixture was stirred at room temperature overnight and then concentrated under reduced pressure to provide the crude product. The residue was purified by flash chromatography (20% ethyl acetate in hexane) to provide the title compound. 1H NMR (CDCl3) δ 7.29-7.43 (m, 5H), 5.13 (s, 2H), 4.15-4.33 (m, 1H), 3.39-3.74 (m, 5H), 3.20-3.37 (m, 1H), 2.84-2.96 (m, 1H), 1.92-2.03 (m, 1H), 1.66-1.82 (m, 1H), 1.46 (s, 9H). MS: (M+H)+ m/z 347.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto provide the crude product
  3. customThe residue was purified by flash chromatography (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-e717cf9abbdd43409d2b38cfaa1fc7a5
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

Loading…