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

HRID 1591732Notes

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-87bdcac45d344061912e8b01cb1a15ff
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291615B2

Reaction notes

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