HCID 69332921, compound → HCID 178501287, compound

HRID 350530Notes

Reaction equation

HRID 350530 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10][C@H:9]1[CH2:17][O:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.CC(O)=O.[Rh]>[C:1]([O:5][C:6]([N:8]1[CH:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10][C@H:9]1[CH2:17][O:18][C@@H:19]1[CH2:28][CH2:27][C@H:22]([C:23]([O:25][CH3:26])=[O:24])[CH2:21][CH2:20]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 69332921HCID 69332921, compound

Product 1

HCID 178501287HCID 178501287, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of methyl 4-[1-tert-butoxycarbonyl-(2S)octahydroindolylmethoxy]benzoate (700 mg, 1.8 mmol) and 5% Rh on alumina (400 mg) in EtOH (10.0 ml) and AcOH (1.0 ml) was hydrogenated at room temperature at 5 atm for 48 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 (7:1, v/v) as eluent to give methyl cis-4-[1-tert-butoxycarbonyl-(2S)-octahydro indolylmethoxy]cyclohexanecarboxylate (600 mg, 85%) as a pale yellow oil. 1H-NMR (CDCl3) δ 1.10–2.35 (m, 20H), 1.44 (s, 9H), 3.45–3.90 (m, 5H), 3.80 (s, 3H).

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 (7:1

Sources & evidence

ORD record
ord-9e1209e516d5448bbb09027df1dfcf56
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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