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

HRID 2059751Notes

Reaction equation

HRID 2059751 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 (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 vacuum to provide the crude product. The residue was purified by chromatography on silica gel (4:1 hexane-EtOAc, eluant) to provide the title compound. 1H NMR (CDCl3) δ 7.29-7.43 (m, 5 H), 5.13 (s, 2 H), 4.15-4.33 (m, 1 H), 3.39-3.74 (m, 5 H), 3.20-3.37 (m, 1 H), 2.84-2.96 (m, 1 H), 1.92-2.03 (m, 1 H), 1.66-1.82 (m, 1 H), 1.46 (s, 9 H). MS: (DCI+) m/z 347 (M+H).

Workup

  1. concentrationconcentrated under vacuum
  2. customto provide the crude product
  3. customThe residue was purified by chromatography on silica gel (4:1 hexane-EtOAc, eluant)

Sources & evidence

ORD record
ord-f947bc426ef74ec999bdf2b58c132068
Source dataset
uspto-grants-2012_10
Patent number
US08278313B2

Reaction notes

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