Ozone → HCID 59532381, compound

HRID 2037546Notes

Reaction equation

HRID 2037546 reaction equation
[CH2:1]([C@@:4]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[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:27]=[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]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)([CH2:1][CH2:2][OH:27])[O:9][C:8]2=[O:10])[CH3:12])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 24823OzoneHCID 4311764Sodium borohydrideHCID 59532366HCID 59532366, compound

Product 1

HCID 59532381HCID 59532381, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-6-allyl-3-((R)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (334 mg, 0.80 mmol) in dry CH2Cl2 (20 mL) was treated with ozone at −78° C. until the reaction mixture became blue. Then the mixture was flushed with oxygen to remove excess ozone. To the above mixture was added NaBH4 (273 mg, 7 mmol) at 0° C. and the reaction mixture was stirred for 4 hrs at ambient temperature under nitrogen. The reaction mixture was washed with water and then extract with CH2Cl2 twice. The combined organic phases were dried over NaSO4, filtered and concentrated to give the residue, which was purified by preparative HPLC to afford (S)-3-((R)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one (118 mg, 35%). 1H NMR (CD3OD): 1.50 (m, 3H), 2.12 (m, 2H), 2.29 (m, 2H), 2.50 (m, 1H), 3.10 (m, 1H), 3.33 (m, 1H), 3.68 (m, 1H), 4.56 (m, 1H), 5.50 (m, 1H), 6.86 (m, 2H), 7.10 (m, 2H), 7.30 (m, 4H).

Workup

  1. customThen the mixture was flushed with oxygen
  2. customto remove excess ozone
  3. washThe reaction mixture was washed with water
  4. extractionextract with CH2Cl2 twice
  5. dry with materialThe combined organic phases were dried over NaSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the residue, which
  9. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-21d4bcbe50bf4a3d81412a38002f5218
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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