Allyl bromide → (R)-N-((S)-1-(3-Bromophenyl)but-3-en-1-yl)-2-methylpropane-2-sulfinamide

Temperature

60 °C

To round bottomed flask equipped with a reflux condensor was charged 161A (2.4673 g, 8.56 mmol), allyl bromide (0.889 mL, 10.27 mmol) and THF (40 mL) to which was added indium (1.180 g, 10.27 mmol) and the mixture heated to 60° C. under nitrogen where it was stirred for overnight. The reaction mixture was quenched by addition of water (40 mL) and the mixture stirred for 15 min, diluted with EtOAc (30 mL), and the phases separated. The aqueous phase was extracted with EtOAc (2×) and the combined organics washed with brine, dried (Na2SO4), filtered and evaporated to give a faint yellow colored oil which was placed under vacuum for overnight to give 161B (3.18 g, 89%). 1H NMR (500 MHz, CDCl3) δ 7.50 (t, J=1.8 Hz, 1H), 7.45-7.42 (m, 1H), 7.27-7.21 (m, 2H), 5.79-5.69 (m, 1H), 5.24-5.22 (m, 1H), 5.22-5.19 (m, 1H), 4.48 (ddd, J=8.1, 5.5, 2.1 Hz, 1H), 3.69 (s, 1H), 2.64-2.58 (m, 1H), 2.47 (dt, J=14.0, 8.4 Hz, 1H), 1.23 (s, 9H).

1. customTo round bottomed flask equipped with a reflux condensor
2. customThe reaction mixture was quenched by addition of water (40 mL)
3. stirringthe mixture stirred for 15 min
4. additiondiluted with EtOAc (30 mL)
5. customthe phases separated
6. extractionThe aqueous phase was extracted with EtOAc (2×)
7. washthe combined organics washed with brine
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. customevaporated
11. customto give a faint yellow colored oil which
12. waitwas placed under vacuum for overnight

ORD record

ord-e0fa0e9baad04113a15301331e900670

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409908B2