Phosphine, triphenyl-, hydrobromide → [(6R*,9aS*)-6-(4-fluorophenyl)-4-oxooctahydropyrido[2,1-c][1,4]oxazin-3-yl]triphenylphosphonium bromide

HRID 1436092Notes

Reaction equation

HRID 1436092 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[N:17]3[C@H:12]([CH2:13][O:14][CH:15](O)[C:16]3=[O:18])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Br-:20].[C:21]1([PH+:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(#N)C>[Br-:20].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[N:17]3[C@H:12]([CH2:13][O:14][CH:15]([P+:27]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:16]3=[O:18])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 517696Phosphine, triphenyl-, hydrobromideHCID 69010340(6R*,9aS*)-6-(4-fluorophenyl)-3-hydroxyhexahydropyrido[2,1-c][1,4]oxazin-4-one

Product 1

HCID 86612604[(6R*,9aS*)-6-(4-fluorophenyl)-4-oxooctahydropyrido[2,1-c][1,4]oxazin-3-yl]triphenylphosphonium bromideYield 98.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (6R*,9aS*)-6-(4-fluorophenyl)-3-hydroxyhexahydropyrido[2,1-c][1,4]oxazin-4-one (26 mg) and triphenylphosphonium bromide (40 mg) in acetonitrile (3 mL) was heated under reflux for one hour and 30 minutes. The reaction solution was left to cool to room temperature, and then the solvent was evaporated under reduced pressure to obtain 57 mg of the title compound. The property value of the compound is as follows.

Workup

  1. temperatureunder reflux for one hour and 30 minutes
  2. waitThe reaction solution was left
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f5dafab9d2304369a11a48200c245442
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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