Triphenylphosphine → HCID 58109155, compound

HRID 2037613Notes

Reaction equation

HRID 2037613 reaction equation
[O:1]=[O+][O-].[CH2:4]([C@@:7]1([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[O:12][C:11](=[O:13])[N:10]([C@H:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])[CH2:9][CH2:8]1)[CH:5]=C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C@:7]2([CH2:4][CH:5]=[O:1])[O:12][C:11](=[O:13])[N:10]([C@H:14]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[CH3:15])[CH2:9][CH2:8]2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24823OzoneHCID 58109553HCID 58109553, compound

Product 1

HCID 58109155HCID 58109155, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ozone was passed into a solution of (R)-6-allyl-6-(4-fluorophenyl)-3-((S)-1-(4-fluorophenyl)ethyl)-1,3-oxazinan-2-one (500 mg, 1.40 mmol) in anhydrous CH2Cl2 (20 mL) at −78° C. until a blue color appeared. Then Ph3P (920 mg, 3.5 mmol) was added at −78° C. The formed mixture was stirred overnight. The mixture was concentrated to give crude 2-((S)-6-(4-fluorophenyl)-3-((S)-1-(4-fluorophenyl)ethyl)-2-oxo-1,3-oxazinan-6-yl)acetaldehyde, which was used for the next step without purification.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-06b13bf9a38547d5aa6646519fe9fe5a
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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