HCID 16093618, compound → HCID 178501289, compound

HRID 350527Notes

Reaction equation

HRID 350527 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.CC(O)=O.[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

5

Reactant 1

HCID 16093618HCID 16093618, compound

Product 1

HCID 178501289HCID 178501289, compoundYield 90.9%

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of methyl 4-(1-tert-butoxycarbonyl-(2S)-pyrrolidinyl)methoxybenzoate (1.0 g, 2.9 mmol) and 5% Rh on alumina (500 mg) in EtOH (10.0 ml) and AcOH (1.0 ml) was hydrogenated at room temperature at 5 atm for 36 hr. The catalyst was filtered off, and the filtrate was concentrated in vacuo. The residue was 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%) as a pale yellow oil. 1H-NMR (CDCl3) δ 1.46 (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 was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel with n-hexane-EtOAc (6:1

Sources & evidence

ORD record
ord-a6092cd7adac4a188e98074a5a4ba62a
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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