Methyl triflate → HCID 12041269, compound

HRID 1823203Notes

Reaction equation

[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:28]OS(C(F)(F)F)(=O)=O.Cl[C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39]>C1COCC1>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@:8]([CH3:28])([C:38]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:39])[C:7](=[O:10])[N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of (2S)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (6.0 g, 24.9 mmol) in THF (100 mL) at −78° C. was added LHMDS (1.0 M in THF, 27.13 mL). After 15 min stirring at −78° C., MeOTf (2.93 mL, 1.05 eq) was added slowly. The mixture was stirred at −78° C. for 30 min before a second portion of LHMDS (27.13 mL) was added. After 20 min stirring, benzyl chloroformate (4.42 mL, 1.25 eq) was added. The mixture was stirred at −78° C. for 2.0 h, and was quenched with 5% citric acid. Removal of solvent, extraction with EtOAC and column chromatography gave the product as a white solid (7.3 g, 75%). 1HNMR (300 MHz, CDCl3) δ 7.38 (m, 5H), 5.2 (m, 2H), 4.6 (m, 1H), 3.8 (s, 3H), 2.87 (dd, 1H, 13.6, 8.8 Hz), 1.88 (dd, 1H, J=13.6; 6.6 Hz), 1.6 (s, 3H), 1.5 (s, 9H).

Workup

additionwas added
stirringAfter 20 min stirring
stirringThe mixture was stirred at −78° C. for 2.0 h
customwas quenched with 5% citric acid
customRemoval of solvent, extraction with EtOAC and column chromatography

Sources & evidence

ORD record: ord-7ba3ce479f404290a7b02ae707695931
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07037911B2

Reaction notes

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