Water → 4-Nitrophenyl 3-(3-ethoxy-1,2,4-oxadiazol-5-yl)-5-[3-fluoro-4-(trifluoromethoxy)phenyl]-piperidine-1-carboxylate

HRID 661242Notes

Reaction equation

[CH2:1]([O:3][C:4]1[N:8]=[C:7]([CH:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[C:17]([F:26])[CH:16]=3)[CH2:12][NH:11][CH2:10]2)[O:6][N:5]=1)[CH3:2].C(N(CC)CC)C.Cl[C:35]([O:37][C:38]1[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=1)=[O:36].O>ClCCl>[CH2:1]([O:3][C:4]1[N:8]=[C:7]([CH:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:23])[F:24])=[C:17]([F:26])[CH:16]=3)[CH2:12][N:11]([C:35]([O:37][C:38]3[CH:39]=[CH:40][C:41]([N+:44]([O-:46])=[O:45])=[CH:42][CH:43]=3)=[O:36])[CH2:10]2)[O:6][N:5]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

195 mg (0.48 mmol) of 3-(3-ethoxy-1,2,4-oxadiazol-5-yl)-5-[3-fluoro-4-(trifluoromethoxy)phenyl]piperidine were initially charged in 4.5 ml of dichloromethane, cooled to 0° C. and admixed with 0.27 ml (193 mg, 1.91 mmol) of triethylamine and 96 mg (0.48 mmol) of 4-nitrophenyl chloroformate. The reaction mixture was stirred at RT for 1 hour and admixed with water, and the organic phase was removed. The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. Yield: 290 mg (94% of theory)

Workup

customthe organic phase was removed
dry with materialThe organic phase was dried over magnesium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-f9ecf270e5c54fddac51961fabd72c0c
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084469B2

Reaction notes

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