Borane;tetrahydrofuran → 4-[(2-Amino-4-chlorophenyl)amino]-1,1,1-trifluoro-2-methylbutan-2-ol

HRID 1500949Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=O)[CH2:11][C:12]([OH:18])([CH3:17])[C:13]([F:16])([F:15])[F:14].B.C1COCC1>C1COCC1>[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][C:12]([CH3:17])([OH:18])[C:13]([F:16])([F:14])[F:15]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of N-(2-amino-4-chlorophenyl)-4,4,4-trifluoro-3-hydroxy-3-methylbutanamide (2.0 g, 6.75 mmol) in THF (30 mL) was added 1.0 M BH3-THF in THF (10 mL). The mixture was stirred at 50° C. overnight. The reaction was quenched by addition of 1 N HCl (15 mL) and the mixture was stirred at room temperature for 1 hour and then washed with EtOAc (30 mL). The resulting aqueous phase was basified to pH 9 with sat. aqueous solution of NaHCO3 and then extracted with EtOAc (30 mL×3). The combined organic phases were washed with brine and then concentrated in vacuo. The residue was purified with flash column (EA:PE=0:1 to 1:1) to afford 4-[(2-amino-4-chlorophenyl)amino]-1,1,1-trifluoro-2-methylbutan-2-ol (0.55 g, yield: 28.8%).

Workup

customThe reaction was quenched by addition of 1 N HCl (15 mL)
stirringthe mixture was stirred at room temperature for 1 hour
washwashed with EtOAc (30 mL)
extractionextracted with EtOAc (30 mL×3)
washThe combined organic phases were washed with brine
concentrationconcentrated in vacuo
customThe residue was purified with flash column (EA:PE=0:1 to 1:1)

Sources & evidence

ORD record: ord-eef2d73e114a43589af8823c8dcf4851
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206191B2

Reaction notes

Loading…