tert-butyl(R)-1-[3-(trifluoromethyl)phenyl]-2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)ethylcarbamate → (5R)-1-(tert-butoxycarbonyl)-5-[3-(trifluoromethyl)phenyl]-2-oxopyrrolidine-3-carboxylic acid

HRID 1972237Notes

Reaction equation

[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([C@H:9]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:10][CH:11]2[C:16](=[O:17])OC(C)(C)[O:13][C:12]2=[O:20])[CH:6]=[CH:7][CH:8]=1>C1(C)C=CC=CC=1>[C:24]([O:23][C:22]([N:21]1[C@@H:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:30])([F:1])[F:29])[CH:4]=2)[CH2:10][CH:11]([C:12]([OH:13])=[O:20])[C:16]1=[O:17])=[O:28])([CH3:26])([CH3:27])[CH3:25]

Participants

Conditions

Temperature: 110 °C

Procedure

The mixture of tert-butyl (R)-1-[3-(trifluoromethyl)phenyl]-2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)ethylcarbamate (520 mg, 1.21 mmol) and toluene (15 mL) is stirred at 110° C. for 3 h. Concentration to give (5R)-1-(tert-butoxycarbonyl)-5-[3-(trifluoromethyl)phenyl]-2-oxopyrrolidine-3-carboxylic acid as a colorless oil. This product is used for the next step without further purification. HPLC-MS calculated for C12H10F3NO3 (M-Boc+H+) 274.06, found 274.10.

Workup

concentrationConcentration

Sources & evidence

ORD record: ord-88470241895a45c6997e8be4aa5cd82d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431607B2

Reaction notes

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