Sodium borohydride → Tert-butyl 2-(hydroxymethyl)-4-(trifluoromethoxy)phenylcarbamate

HRID 641588Notes

Reaction equation

[CH:1]([C:3]1[CH:8]=[C:7]([O:9][C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:5][C:4]=1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:8]=[C:7]([O:9][C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:5][C:4]=1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20]

Participants

Conditions

Temperature: 0 °C

Procedure

A magnetically stirred solution of tert-butyl 2-formyl-4-(trifluoromethoxy)phenylcarbamate (18.36 g, 60.14 mmol) in methanol (200 mL) was treated with sodium borohydride (2.3 g, 60.14 mmol), the mixture was quickly cooled in a dry ice/acetone bath, then allowed to warm to 0° C., and stirred for 1 h. The reaction was quenched with water (50 mL), the methanol was stripped, and the aqueous was extracted with diethyl ether (300 mL). The organic phase was washed successively with saturated ammonium chloride (2×100 mL), water (100 mL), and brine (100 mL), dried over sodium sulfate, and concentrated in-vacuo to a colorless solid, which was used as-is in the next step. 1H NMR (500 MHz, DMSO) δ ppm 1.46 (s, 9 H) 4.52 (d, J=5.50 Hz, 2 H) 5.55 (m, 1 H) 7.21 (d, J=8.80 Hz, 1 H) 7.34 (s, 1 H) 7.59 (d, J=8.25 Hz, 1 H) 8.68 (s, 1 H).

Workup

temperaturethe mixture was quickly cooled in a dry ice/acetone bath
customThe reaction was quenched with water (50 mL)
extractionthe aqueous was extracted with diethyl ether (300 mL)
washThe organic phase was washed successively with saturated ammonium chloride (2×100 mL), water (100 mL), and brine (100 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated in-vacuo to a colorless solid, which

Sources & evidence

ORD record: ord-e9107afccaed40b99ed59db0277aa83c
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696205B2

Reaction notes

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