Triacetoxyperiodinane → benzyl (S)-1-((1S,2S)-2-isopropyl-4-oxocyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

HRID 1171536Notes

Reaction equation

[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:9]2=[O:24])[C@H:4]([CH:25]([CH3:27])[CH3:26])[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:25]([C@@H:4]1[CH2:3][C:2](=[O:1])[CH2:7][CH2:6][C@@H:5]1[N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]1=[O:24])([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 0 °C

Procedure

Benzyl (S)-1-((1S,2S,4R)-4-hydroxy-2-isopropylcyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (333 mg) was dissolved in CH2Cl2 (5 mL) and cooled to 0° C. prior to the addition of Dess-Martin reagent (678.9 mg). This solution was warmed to rt over 1 h, and then was cooled to 0° C. prior to the addition of more Dess-Martin reagent (260 mg). After 1 h at rt, the reaction was quenched with Et2O and 1N NaOH. The organic extracts were combined, washed with saturated Na2S2O3 and NaHCO3 solutions, dried (MgSO4), filtered, and concentrated to afford benzyl (S)-1-((1S,2S)-2-isopropyl-4-oxocyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (350 mg). MS found: (M+H)+=373.4.

Workup

temperatureThis solution was warmed to rt over 1 h
temperaturewas cooled to 0° C.
customthe reaction was quenched with Et2O and 1N NaOH
washwashed with saturated Na2S2O3 and NaHCO3 solutions
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-1d331352925e462ab47fb83da0ef0acb
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829571B2

Reaction notes

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