Ozone → HCID 178523822, compound

HRID 271339Notes

Reaction equation

HRID 271339 reaction equation
[CH2:1]([O:8][C:9](=[O:34])[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([O:17][CH2:18][C:19]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])=CC2C=CC=CC=2)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:35]=[O+][O-]>ClCCl.CO>[F:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH:19]([OH:35])[CH2:18][O:17][C@H:14]1[CH2:15][CH2:16][C@H:11]([NH:10][C:9](=[O:34])[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 24823Ozone2×HCID 178523819HCID 178523819, compound

Product 1

HCID 178523822HCID 178523822, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 41 g of trans-[4-(2-(2-fluorophenyl)-3-phenyl-allyloxy)-cyclohexyl]-carbamic acid benzyl ester in 750 mL of dichloromethane and 250 mL of methanol cooled to −78° C. was dispersed a stream of ozone from an ozone generator until a blue color persisted. The excess ozone was purged with nitrogen until the blue color dissipated, and 7.8 g of sodium borohydride was added. After warming to room temperature over 30 min, the solution was diluted with 50 mL of water and concentrated under reduced pressure. The residue was treated with 500 mL of 3N hydrochloric acid and extracted into 3×500 mL of ethyl acetate. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. Chromatography over silica gel eluting with a gradient of 2%-30% ethyl acetate in hexane gave 30 g of product as a white crystalline solid: MS (m+1)=388.4; 1H NMR (400 MHz, CDCl3) 7.53 (m, 1H), 7.33 (m, 5H), 7.25 (m, 1H), 7.14 (m, 1H), 7.0 (m, 1H), 5.15 (d, 1H), 5.07 (s, 2H), 4.6 (m, 1H), 3.7 (d, 1H), 3.5 (br m, 1H), 3.4 (t, 1H), 3.3 (m, 1H), 2.9 (s, 1H), 2.0 (m, 4H), 1.2 (q, 2H), 1.15 (q, 2H).

Workup

  1. customThe excess ozone was purged with nitrogen until the blue color
  2. addition7.8 g of sodium borohydride was added
  3. additionthe solution was diluted with 50 mL of water
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was treated with 500 mL of 3N hydrochloric acid
  6. extractionextracted into 3×500 mL of ethyl acetate
  7. dry with materialThe combined extracts were dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1539926626624c13a818f4a6a9d51d57
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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