Borane;tetrahydrofuran → HCID 13626979, compound

HRID 1061271Notes

Reaction equation

[Br:1][C:2]1[CH:6]=[C:5]([C:7](=[O:10])[CH2:8][Br:9])[O:4][N:3]=1.B.C1COCC1>>[Br:9][CH2:8][C@@H:7]([C:5]1[O:4][N:3]=[C:2]([Br:1])[CH:6]=1)[OH:10]

Participants

Reactant 2

HCID 2723981Borane;tetrahydrofuran

HCID 136269733-Bromo-5-(bromoacetyl)isoxazole

Product 1

HCID 13626979HCID 13626979, compound

Procedure

The title compound was prepared from 3-bromo-5-(bromoacetyl)isoxazole (which was obtained in Example 118), (R)-2-methyl-CBS-oxaborolidine monohydrate, and 1M BH3/THF solution in substantially the same manner, as described in Example 103 with one change; the crude product was purified by flash chromatography and reverse phase chromatography to give a colorless oil (1.45 g, 16% yield): 1H NMR (300 MHz, CDCl3) δ 3.67 - 3.81 (m, 2H), 5.16. (m, 1H), 6.49 (s, 1H).

Workup

customthe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-4f73c531a9094a73b0bb83c4365e19bb
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525202B2

Reaction notes

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