(Dimethyl sulfide)trihydroboron → tert-butyl N-[1-[3-(hydroxymethyl)phenyl]ethyl]carbamate

HRID 467503Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14](O)=[O:15])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].B.CSC>C1COCC1>[OH:15][CH2:14][C:13]1[CH:12]=[C:11]([CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH3:10])[CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-[1-(tert-Butoxycarbonylamino)ethyl]benzoic acid (7.57 g, 28.53 mmol) was dissolved in anhydrous THF (45 mL) and 2M borane-dimethylsulfide in THF (42.8 mL, 85.6 mmol) was added dropwise at ambient temperature. The reaction was stirred at this temperature for 3 hours then cooled to 0° C. and quenched with MeOH. The solvents were removed under reduced pressure and the resulting residue partitioned between 1M HCl and ethyl acetate. The organic layer was washed with saturated sodium bicarbonate (×1) and brine (×1), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™ eluting with 0 to 30% EtOAc/petroleum ether) to give the sub-title compound as a white solid (4.91 g, 68% Yield). 1H NMR (400 MHz, DMSO) δ 1.28 (d, 3H), 1.36 (s, 9H), 4.47 (d, 2H), 4.54-4.64 (m, 1H), 5.17 (t, 1H), 7.14 (d, 2H), 7.23 (d, 2H) and 7.38 (d, 1H) ppm; MS (ES+) 252.3.

Workup

customquenched with MeOH
customThe solvents were removed under reduced pressure
customthe resulting residue partitioned between 1M HCl and ethyl acetate
washThe organic layer was washed with saturated sodium bicarbonate (×1) and brine (×1)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (ISCO Companion™ eluting with 0 to 30% EtOAc/petroleum ether)

Sources & evidence

ORD record: ord-1e359becd0b1414788764079aa424676
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08623869B2

Reaction notes

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