Lithium tri-s-butylborohydride → HCID 88875568, compound

To a solution of 31 (1.30 g, 5 mmol) in hexanes (30 mL) which was cooled down to −78° C. under N2, L-selectride (20 mL, 10 mmol) was added dropwise. The resulting mixture was further stirred at this temperature for 1 h, and then quenched with brine and diluted with EtOAc (100 mL). The organic layers were washed with brine, dried, and evaporated. The obtained residue was chromatographed on silica gel eluted with EtOAc/hexanes (0-20%) to obtain 0.80 g (31%) of 32 as a yellowish oil. NMR (CD3OD) δ 1.21 (3 H, s), 1.22 (3 H, s), 3.68 (1 H, dd, J=6.36, 8.36 Hz), 3.84 (1 H, dd, J=6.78, 8.52 Hz), 4.00 (1 H, m), 4.23 (1 H, m), 4.70 (1 H, d, J=5.04 Hz), 7.68 (1 H, dd, J=1.52, 9.20 Hz), 8.15 (1 H, d, J=1.96 Hz); LC/MS (M+1) 262.

1. customquenched with brine
2. additiondiluted with EtOAc (100 mL)
3. washThe organic layers were washed with brine
4. customdried
5. customevaporated
6. customThe obtained residue was chromatographed on silica gel
7. washeluted with EtOAc/hexanes (0-20%)

ORD record

ord-679e7d70b58e4afc876173581b04fb6f

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921373B2