Lithium borohydride → [3-(2-Hydroxy-ethyl)-benzyl]-[2-(2-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester

HRID 553313Notes

Reaction equation

C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][N:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[OH:21])[CH:6]=1.[BH4-].[Li+]>O1CCCC1>[C:25]([O:24][C:22](=[O:23])[N:12]([CH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([CH2:4][CH2:3][OH:2])[CH:6]=1)[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21])([CH3:26])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of [3-({tert-butoxycarbonyl-[2-(2-hydroxy-phenyl)-ethyl]-amino}-methyl)-phenyl]-acetic acid methyl ester (560 mg) in anhydrous tetrahydrofuran (20 mL) was treated with lithium borohydride (62 mg) and the mixture was heated at 60° C. for 5 hours under nitrogen. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and saturated aqueous brine, the organic layer was separated, dried and the solvent evaporated under reduced pressure. The residue was purified on silica, eluting with 40% ethyl acetate in isohexane to yield the sub-titled compound (500 mg).

Workup

temperatureThe reaction mixture was cooled to room temperature
custompartitioned between ethyl acetate and saturated aqueous brine
customthe organic layer was separated
customdried
customthe solvent evaporated under reduced pressure
customThe residue was purified on silica
washeluting with 40% ethyl acetate in isohexane

Sources & evidence

ORD record: ord-bce85c8b7231465e9d8fa5ceb042391e
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951954B2

Reaction notes

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