Ammonium Chloride → Tert-butyl 3-chloro-4-(3-hydroxycyclohexyl)benzoate

HRID 1849763Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH2:16]1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[Na].[Cl-].[NH4+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH:17]([OH:21])[CH2:16]1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of tert-butyl 3-chloro-4-(3-oxocyclohexyl)benzoate in anhydrous methanol (50 mL) was added sodium borobydride (1.04 g, 27.40 mmol) at 0° C. The reaction mixture was stirred for 1 hour at 0° C., after which saturated ammonium chloride solution (10 mL) was added. All volatiles were evaporated under reduced pressure, and the residue was partitioned between ethyl acetate (200 mL) and water (20 mL). The organic phase was washed with brine (10 mL), dried over sodium sulfate, and filtered. Concentration under reduced pressure gave a residue which was purified by silica gel column chromatography using 0-40% ethyl acetate in hexanes as eluent to afford the title compound as colorless oil (2.24 g, 53%): 1H NMR (300 MHz, CDCl3) δ 7.94-7.92 (m, 1H), 7.84-7.79 (m, 1H), 7.32-7.27 (m, 1H), 3.85-3.69 (m, 1H), 3.16-3.03 (m, 1H), 2.19-2.04 (m, 2H), 1.96-1.77 (m, 2H), 1.63-1.18 (m, 14H); MS (ES+) m/z 255.2, 257.1 (M−55).

Workup

customAll volatiles were evaporated under reduced pressure
customthe residue was partitioned between ethyl acetate (200 mL) and water (20 mL)
washThe organic phase was washed with brine (10 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationConcentration under reduced pressure
customgave a residue which
customwas purified by silica gel column chromatography

Sources & evidence

ORD record: ord-d314e415009d49d2ba5b6c004fdc9f4a
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952169B2

Reaction notes

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