Hydrogen Peroxide → (1R,3R)-methyl 1-(benzyloxycarbonylamino)-3-(4-(2-hydroxyethyl)phenyl)cyclopentanecarboxylate

HRID 1511866Notes

Reaction equation

B1C2CCCC1CCC2.[CH2:10]([O:17][C:18]([NH:20][C@:21]1([C:34]([O:36][CH3:37])=[O:35])[CH2:25][CH2:24][C@@H:23]([C:26]2[CH:31]=[CH:30][C:29]([CH:32]=[CH2:33])=[CH:28][CH:27]=2)[CH2:22]1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.B([O-])[O-:39].[OH-].[Na+].OO>C1COCC1>[CH2:10]([O:17][C:18]([NH:20][C@:21]1([C:34]([O:36][CH3:37])=[O:35])[CH2:25][CH2:24][C@@H:23]([C:26]2[CH:27]=[CH:28][C:29]([CH2:32][CH2:33][OH:39])=[CH:30][CH:31]=2)[CH2:22]1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

9-BBN (25 ml, 12.50 mmol) was added dropwise to a stirred and cooled solution of (1R,3R)-methyl 1-(benzyloxycarbonylamino)-3-(4-vinylphenyl)cyclopentanecarboxylate (0.682 g, 1.797 mmol) in THF (15 mL). The reaction mixture was checked by TLC to ensure complete conversion to boronate. Once complete the ice bath was removed and stirring was continued overnight. The reaction mixture was cooled to 0° C. and methanol (20 ml) was added. Aqueous NaOH (7.30 ml, 14.59 mmol) and H2O2 (1.522 ml, 14.90 mmol) were poured into the reaction mixture. Stirring was continued for 2 hours. The solvent was removed under reduced pressure and the product purified by FCC to afford (1R,3R)-methyl 1-(benzyloxycarbonylamino)-3-(4-(2-hydroxyethyl)phenyl)cyclopentanecarboxylate (0.507 g, 1.276 mmol, 71.0% yield) as colorless oil.

Workup

customOnce complete the ice bath was removed
stirringstirring
additionmethanol (20 ml) was added
stirringStirring
waitwas continued for 2 hours
customThe solvent was removed under reduced pressure
customthe product purified by FCC

Sources & evidence

ORD record: ord-9c2891a94cdb4a66bc71acb7475415ad
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217027B2

Reaction notes

Loading…