Borane;tetrahydrofuran → HCID 69655076, compound

HRID 1061266Notes

Reaction equation

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

Participants

Reactant 2

HCID 2723981Borane;tetrahydrofuran

HCID 15592151N-(4-(2-bromoacetyl)phenyl)methanesulfonamide

Product 1

HCID 69655076HCID 69655076, compound

Procedure

The title compound was prepared from N-[4-(2-bromoacetyl)phenyl]methanesulfonamide (0.23 g, 0.82 mmol )(which was obtained in Example 111), and 1M BH3/THF solution (10.35 mL, 10.5 mmol) in substantially the same manner, as described in Example 103 and was obtained as a white solid (1.75 g, 72% yield); MS (ES) m/z: 293 (M)+; 1H NMR (400 MHz, DMSO-d6) δ 7.14 (d, 2H), 2.95 (s, 3H), 3.53 (m, 1H), 3.55 (m, 1H), 4.73, (m, 1H), 5.75 (d, 1H), 7.14 (d, 2H), 9.74 (s, 1H).

Sources & evidence

ORD record: ord-296a05b52d4e4985b3ff098e1579536e
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525202B2

Reaction notes

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