Sodium borohydride → HCID 86593507, compound

To a solution of 6a (420 mg, 1.4 mmol) in methanol (10 mL) was added NaBH4 (531 mg, 14.0 mmol) in small portions. The reaction mixture was stirred at room temperature for 1 h before removal of the solvent. The residue was partitioned between 100 mL of ethyl acetate and 50 mL of water. The aqueous layer was extracted with 100 mL of ethyl acetate. The combined organic layers were dried over Na2SO4 and concentrated to yield 357 mg of the desired product as a white solid (94%). 1H NMR (300 MHz, CDCl3) δ 4.74 (m, 1H), 3.71 (m, 2H), 3.58 (m, 1H), 2.31 (m, 1H), 2.14 (m, 1H), 1.92 (m, 1H), 145 (s, 9H), 1.17 (d, 3H, J=7.0 Hz). 13C NMR (75.5 MHz, CDCl3) δ 156.26 (C═O), 128.41 (q, CF3, 1JCF=279.4 Hz), 80.14 (C), 64.78 (CH2), 50.73 (CH), 35.59 (q, CH, 2JCF=29.6 Hz), 31.74 (CH2), 28.52 (3×CH3), 13.71 (CH3); 19F NMR (282.6 MHz, CDCl3/CFCl3) δ −73.84 (br. s, 3F); GC-MS (CI, CH4): 272 (100, [M+1]+), 216 (68), 172 (26), 57 (11).

1. customThe residue was partitioned between 100 mL of ethyl acetate and 50 mL of water
2. extractionThe aqueous layer was extracted with 100 mL of ethyl acetate
3. dry with materialThe combined organic layers were dried over Na2SO4
4. concentrationconcentrated

ORD record

ord-69d7e914e6c447099a7d7210ad1cb5ff

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07371867B2