(4aS-cis-)-6-benzyl-octahydropyrrolo(3.4-b)pyridine → (4aS,7aS)-tert-butyl 6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate

HRID 2356382Notes

Reaction equation

HRID 2356382 reaction equation
[CH2:1]([N:8]1[CH2:16][C@@H:15]2[C@@H:10]([CH2:11][CH2:12][CH2:13][NH:14]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC([O-])=O)([O:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=O)=O>CO>[CH2:1]([N:8]1[CH2:16][C@@H:15]2[C@@H:10]([CH2:11][CH2:12][CH2:13][N:14]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10198297(4aS-cis-)-6-benzyl-octahydropyrrolo(3.4-b)pyridineHCID 86600350tert-Butoxycarbonyl dicarbonate

Product 1

HCID 29973012(4aS,7aS)-tert-butyl 6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylateYield 97.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The preparation comprises stirring [1S,6S]-8-benzyl-2,8-diazabicyclo[4,3,0]nonane (5.0 g, 23.1 mmol) in methanol (50 mL) at room temperature, adding batchwise tertbutyloxycarbonyl dicarbonate (5.1 g, 23.4 mmol), stirring for 0.5 h, vacuum distilling to remove solvent, and column chromatographing with petroleum ether and ethyl, acetate at the ratio of 10:1 to give [1S,6S]-8-benzyl-2-tertbutyloxycarbonyl-2,8-diazabicyclo[4,3,0]nonane (7.1 g, 97.2%), [α]20D=−72.4° (CHCl3, C=5).

Workup

  1. distillationvacuum distilling
  2. customto remove solvent, and column chromatographing with petroleum ether and ethyl, acetate at the ratio of 10:1

Sources & evidence

ORD record
ord-c5f83b656f624b4bb5c4bcbce28be9d5
Source dataset
uspto-grants-2010_07
Patent number
US07759362B2

Reaction notes

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