Triethylamine → 3-Methyl 1-(4-nitrophenyl) 5-[3-fluoro-4-(trifluoromethoxy)phenyl]piperidine-1,3-dicarboxylate

HRID 661261Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:13]2[CH2:18][NH:17][CH2:16][CH:15]([C:19]([O:21][CH3:22])=[O:20])[CH2:14]2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].C(N(CC)CC)C.Cl[C:31]([O:33][C:34]1[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][CH:35]=1)=[O:32]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:13]2[CH2:18][N:17]([C:31]([O:33][C:34]3[CH:35]=[CH:36][C:37]([N+:40]([O-:42])=[O:41])=[CH:38][CH:39]=3)=[O:32])[CH2:16][CH:15]([C:19]([O:21][CH3:22])=[O:20])[CH2:14]2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:10])[F:11]

Participants

Conditions

Temperature: 0 °C

Procedure

1.74 g (5.42 mmol) of the compound from Example 92A were initially charged in 80 ml of dichloromethane and cooled to 0° C., and admixed with 1.5 ml (1.09 g, 10.8 mmol) of triethylamine and 1.09 g (5.42 mmol) of 4-nitrophenyl chloroformate. The reaction mixture was allowed to warm up slowly to RT and stirred at RT for 16 h. It was washed repeatedly with water, dried over sodium sulphate, filtered and concentrated under reduced pressure. Yield: 2.4 g (87% of theory)

Workup

temperatureto warm up slowly to RT
washIt was washed repeatedly with water
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0e745cd4eb5a49879e56ebf8845e8713
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084469B2

Reaction notes

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