Methanol → (4-Isobutoxy-3-{[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl}phenyl)methanol

HRID 507942Notes

Reaction equation

[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=1[CH2:14][N:15]([CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:16]1[S:17][CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:20]=1)[CH:2]([CH3:4])[CH3:3].CO.O1CCCC1.[BH4-].[Na+]>C(OCC)(=O)C>[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][C:7]=1[CH2:14][N:15]([CH2:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:16]1[S:17][CH:18]=[C:19]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:20]=1)[CH:2]([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 4-isobutoxy-3-{[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl}benzaldehyde (1.43 g, 3.04 mmol), methanol (5 mL) and tetrahydrofuran (10 mL) was added sodium borohydride (58 mg, 1.52 mmol) under stirring at 0° C., and the mixture was stirred at the same temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-1/1) to give the title compound (1.28 g, yield 88%) as colorless crystals.

Workup

stirringthe mixture was stirred at the same temperature for 2 hr
washwashed with water and saturated brine
customdried
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-1/1)

Sources & evidence

ORD record: ord-c46fe404ed2e4fe48f0e7a742ced5b54
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786165B2

Reaction notes

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