HCID 76540720, compound → Racemic (3aSR,6aSR)-6a-(5-Bromo-2-fluorophenyl)hexahydrofuro[3,4-c]isoxazole

HRID 2060750Notes

Reaction equation

HRID 2060750 reaction equation
[CH2:1]([O:4][CH2:5][C:6]([C:9]1[CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][C:10]=1[F:16])=[N:7][OH:8])[CH:2]=[CH2:3]>C1(C)C(C)=CC=CC=1>[Br:15][C:13]1[CH:12]=[CH:11][C:10]([F:16])=[C:9]([C:6]23[CH2:5][O:4][CH2:1][CH:2]2[CH2:3][O:8][NH:7]3)[CH:14]=1

Participants

3

Reactant 1

HCID 76540720HCID 76540720, compound

Product 1

HCID 57475807Racemic (3aSR,6aSR)-6a-(5-Bromo-2-fluorophenyl)hexahydrofuro[3,4-c]isoxazoleYield 72%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 2-(allyloxy)-1-(5-bromo-2-fluorophenyl)ethanone oxime (120 g, 417 mmol) in xylene (2 L) is heated at 140° C. for 6 h. The reaction is cooled and the solvent is removed under reduced pressure to give a solid. The solid is purified by trituration with 9:1 hexanes/MTBE to give the title compound (85 g, 72%). ES/MS m/e (79Br/81Br) 288, 290 (M+1).

Workup

  1. temperatureThe reaction is cooled
  2. customthe solvent is removed under reduced pressure
  3. customto give a solid
  4. customThe solid is purified by trituration with 9:1 hexanes/MTBE

Sources & evidence

ORD record
ord-74f7f81091214934bcd9299e7c7ddc98
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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