Ozone → (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-hydroxyethyl)-6-phenyl-1,3-oxazinan-2-one
Reaction equation
[CH2:1]([C@@:4]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=C.[O:26]=[O+][O-].[BH4-].[Na+]>C(Cl)Cl>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([C@@H:11]([N:7]2[CH2:6][CH2:5][C@:4]([CH2:1][CH2:2][OH:26])([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[O:9][C:8]2=[O:10])[CH3:12])=[CH:14][CH:15]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (R)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (3 g, 7.5 mmol) in CH2Cl2 (50 mL) was treated with O3 at −78° C. till the mixture turned blue. Then NaBH4 (285 mg, 75 mmol) was added to the solution at 0° C., and the reaction solution was stirred at room temperature for 3 hours. The reaction was quenched by H2O, and the mixture was extracted with EtOAc. The combined organic phase was concentrated to give the crude product, which was purified by preparative TLC to give (S)-3-((S)-1-(4-bromo-phenyl)ethyl)-6-(2-hydroxyethyl)-6-phenyl-1,3-oxazinan-2-one (2.5 g, 84%). 1H NMR (CDCl3): 1.48 (t, 3H), 2.05-2.41 (m, 4H), 2.71-2.92 (m, 2H), 3.51 (m, 1H), 3.71 (m, 1H), 5.58 (m, 1H), 6.73 (d, 2H), 7.12 (m, 2H), 7.23-7.45 (m, 6H).
Workup
- customThe reaction was quenched by H2O
- extractionthe mixture was extracted with EtOAc
- concentrationThe combined organic phase was concentrated
- customto give the crude product, which
- customwas purified by preparative TLC
Sources & evidence
- ORD record
- ord-ffbf8da422c240a49956b89adc188663
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575157B2
Reaction notes
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