HCID 16093618, compound → HCID 178501289, compound

HRID 354461Notes

Reaction equation

HRID 354461 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Rh]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C@@H:15]1[CH2:24][CH2:23][C@H:18]([C:19]([O:21][CH3:22])=[O:20])[CH2:17][CH2:16]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 16093618HCID 16093618, compound

Product 1

HCID 178501289HCID 178501289, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

Methyl 4-(1-tert-butoxycarbonyl-(2S)-pyrrolidinyl)methoxybenzoate (1.0 g, 2.9 mmol) and 5% Rh on alumina (500 mg) in 10 ml EtOH/1 ml AcOH was hydrogenated at rt at 5 atm for 36 hr. The catalyst filtered off, the filtrate concentrated in vacuo and the residue purified by column chromatography on silica gel with n-hexane-EtOAc (6:1, v/v) as eluent to give methyl cis-4-[(1-tert-butoxycarbonyl-(2S)-pyrrolidinyl)methoxy]cyclohexanecarboxylate (900 mg, 89%) pale yellow oil. 1H-NMR (CDCl3) δ1.46(s,9H),1.46-2.00(m,12H),2.34(m,1H),3.20-3.55 (m,5H),3.67(s,3H), 3.84-3.92(m,1H).

Workup

  1. filtrationThe catalyst filtered off
  2. concentrationthe filtrate concentrated in vacuo
  3. customthe residue purified by column chromatography on silica gel with n-hexane-EtOAc (6:1

Sources & evidence

ORD record
ord-92047807cbc44600a10c2a0a3741c6d7
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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