Boron tribromide → HCID 22087109, compound

HRID 2227435Notes

Reaction equation

HRID 2227435 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C@@H:14]3[O:18][C:17](=[O:19])[N:16]([C:20]4[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=4)[CH2:15]3)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C@@H:14]3[O:18][C:17](=[O:19])[N:16]([C:20]4[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=4)[CH2:15]3)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 9865613HCID 9865613, compound

Product 1

HCID 22087109HCID 22087109, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1 g of (5S)-(−)-5-[4-(4-fluorobenzyl)-1-piperidinylmethyl]-3-(4-methoxyphenyl)-oxazolidin-2-one [obtainable by reaction of (5R)-(−)-5-(methanesulfonyloxymethyl)-3-p-methoxyphenyloxazolidin-2-one with 4- (4-fluorobenzyl)piperidine hydrochloride] in 25ml of dichloromethane is mixed with equimolar amounts of boron tribromide and stirred for 1 hour. Usual work-up gives (5S)-(−)-5-[4-(4-fluorobenzyl)-1-piperidinylmethyl]-3-(4-hydroxyphenyl)-oxazolidin-2-one,

Sources & evidence

ORD record
ord-4a57cfa839214341ba9045433d8247e7
Source dataset
uspto-grants-2002_07
Patent number
US06413989B1

Reaction notes

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