Dimethylcarbamoyl Chloride → HCID 66877221, compound

HRID 503962Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)(=[O:21])=[O:20])=[CH:15][C:14]=2[CH2:29][OH:30])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].CC([N-]C(C)C)C.[CH3:39][N:40]([CH3:44])[C:41](Cl)=[O:42]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)(=[O:21])=[O:20])=[CH:15][C:14]=2[CH2:29][O:30][C:41](=[O:42])[N:40]([CH3:44])[CH3:39])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -78 °C

Procedure

3-[4-(3-Fluoro-benzenesulfonyl)-2-hydroxymethyl-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (74 mg, 0.170 mmol) was dissolved in 25 ml of THF and the mixture was cooled to −78° C. LDA (0.102 ml, 0.204 mmol) was added and allowed to stir for 30 minutes. Dimethylcarbamoyl chloride (0.023 ml, 0.255 mmol) was added and the mixture was allowed to warm to room temperature over 3 hours. The mixture was diluted with water and extracted with EtOAc. The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH 95/5) to give 83 mgs (96%) of 3-[2-Dimethylcarbamoyloxymethyl-4-(3-fluoro-benzenesulfonyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as a clear oil.

Workup

temperatureto warm to room temperature over 3 hours
extractionextracted with EtOAc
dry with materialThe combined organic extracts were dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography (CH2Cl2/MeOH 95/5)

Sources & evidence

ORD record: ord-09108ef9ada14be6ba19b3feb30419c6
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776910B2

Reaction notes

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