Ozone → HCID 71215526, compound

HRID 271366Notes

Reaction equation

HRID 271366 reaction equation
[CH2:1]([O:8][C:9](=[O:33])[NH:10][C@H:11]1[CH2:15][CH2:14][C@H:13]([O:16][CH2:17][C:18]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)=CC2C=CC=CC=2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:34]=[O+][O-]>ClCCl>[CH2:1]([O:8][C:9](=[O:33])[NH:10][C@H:11]1[CH2:15][CH2:14][C@H:13]([O:16][CH2:17][C:18](=[O:34])[C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24823Ozone2×HCID 86760758HCID 86760758, compound

Product 1

HCID 71215526HCID 71215526, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 10 g of trans [3-(3-phenyl-2-p-tolyl-allyloxy)-cyclopentyl]-carbamic acid benzyl ester in 500 mL of dichloromethane 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 20 mL of methyl sulfide was added. After warming to room temperature over 30 min, the solution was concentrated under reduced pressure. Chromatography over silica gel eluting with a gradient of 5%-45% ethyl acetate in hexane gave 6.5 g of product as a white crystalline solid: MS (m+1)=368.3; 1H NMR (400 MHz, CDCl3) 7.35 (m, 2H), 7.1 (m, 5H), 7.0 (m, 2H), 5.1 (s, 2H), 4.7 (m, 1H), 4.2 (s, 2H), 4.1 (m, 1H), 2.35 (s, 3H), 2.2 (m, 2H), 1.95 (m, 1H), 1.74 (m, 1H), 1.6 (m, 1H), 1.4 (m, 1H).

Workup

  1. customThe excess ozone was purged with nitrogen until the blue color
  2. addition20 mL of methyl sulfide was added
  3. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-85c504d97c81436fb860aa9b4a7ceb8e
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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