HCID 86658713, compound → HCID 178461792, compound

HRID 2368150Notes

Reaction equation

[OH:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][C@@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1>CO.[C].[Rh]>[OH:1][C@@H:2]1[CH2:19][CH2:18][C@H:5]([O:6][CH2:7][C@@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of tert-butyl [(1S)-2-(4-hydroxyphenoxy)-1-methylethyl]carbamate (40 g) and 5% rhodium-carbon (containing water (50%), 8.0 g) in methanol (600 mL) was stirred at 60° C. for 3 hr under a hydrogen atmosphere (5 atm). The catalyst was removed by filtration, and the filtrate was concentrated. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (8.3 g).

Workup

customThe catalyst was removed by filtration
concentrationthe filtrate was concentrated
customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-e94b44c52d67414faf66a0de955737e8
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703758B2

Reaction notes

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