Carbon Dioxide → HCID 57546035, compound

HRID 913895Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:21][O:22][CH:23]([C:25]3[CH:26]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:28]=[C:29]4[C:33]=3[N:32](C)[CH:31]=[CH:30]4)[CH3:24])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(=O)=O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:21][O:22][CH:23]([C:25]3[CH:26]=[C:27]([C:35]([F:37])([F:36])[F:38])[CH:28]=[C:29]4[C:33]=3[NH:32][CH:31]=[CH:30]4)[CH3:24])[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 280Carbon Dioxide

HCID 57546189HCID 57546189, compound4×

Product 1

HCID 57546035HCID 57546035, compound

Procedure

Enantiomers A and B of tert-butyl 4-(4-fluorophenyl)-4-((1-(1-methyl-5-(trifluoromethyl)-1H-indol-7-yl)ethoxy)methyl)piperidine-1-carboxylate. (±)-tert-butyl 4-(4-fluorophenyl)-4-((1-(1-methyl-5-(trifluoromethyl)-1H-indol-7-yl)ethoxy)methyl)piperidine-1-carboxylate (derived from tert-Butyl 4-(4-fluorophenyl)-4-((1-(5-(trifluoromethyl)-1H-indol-7-yl)ethoxy)methyl)piperidine-1-carboxylate by methylation) was subjected to chiral HPLC on a chiralcel OD-H column with a mobile phase of 95% CO2/5% ethanol/0.1% diethylamine. The early-eluting enantiomer is Enantiomer A of tert-butyl 4-(4-fluorophenyl)-4-((1-(1-methyl-5-(trifluoromethyl)-1H-indol-7-yl)ethoxy)methyl)piperidine-1-carboxylate and the late-eluting enantiomer is Enantiomer B of tert-butyl 4-(4-fluorophenyl)-4-((1-(1-methyl-5-(trifluoromethyl)-1H-indol-7-yl)ethoxy)methyl)piperidine-1-carboxylate.

Sources & evidence

ORD record: ord-0d619244c27344eead6f45a10627a5e9
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026257B2

Reaction notes

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