Boron tribromide → HCID 58109237, compound

HRID 2037678Notes

Reaction equation

HRID 2037678 reaction equation
[CH2:1]([C@@:4]1([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([C@@:4]1([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58109563HCID 58109563, compound

Product 1

HCID 58109237HCID 58109237, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-6-allyl-6-(4-fluorophenyl)-3-((S)-1-(4-methoxyphenyl)ethyl)-1,3-oxazinan-2-one (1.5 g, 4.07 mmol) in CH2Cl2 (40 mL) was added BBr3 (3 g, 12.2 mmol) at −78° C. The mixture was stirred at this temperature for 2 h. The solution was washed with satd aq NaHCO3 and the aqueous layer was extracted with CH2Cl2. The organic layer was dried over Na2SO4 and concentrated to give (R)-6-allyl-6-(4-fluorophenyl)-3-((S)-1-(4-hydroxyphenyl)ethyl)-1,3-oxazinan-2-one (1.2 g, 83%), which was used for the next step without further purification.

Workup

  1. washThe solution was washed with satd aq NaHCO3
  2. extractionthe aqueous layer was extracted with CH2Cl2
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a6235c72131441a6b2a42ea31799a96b
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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