4-Fluorophenyl chloroformate → [(3S,4R)-1-Benzyl-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester

HRID 587401Notes

Reaction equation

HRID 587401 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:32])[N:10]([C@H:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][C:20](Cl)=[C:19](Cl)[CH:18]=3)[CH2:15][N:14]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:13]2)[CH3:11])=[CH:4][CH:3]=1.C(N1C[C@@H](C2C=CC([F:51])=CC=2)[C@H](NC)C1)C1C=CC=CC=1.ClC(OC1C=CC(F)=CC=1)=O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:32])[N:10]([C@H:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][C:20]([F:51])=[CH:19][CH:18]=3)[CH2:15][N:14]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:13]2)[CH3:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 27332564-Fluorophenyl chloroformateHCID 58303163[(3S,4R)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl esterHCID 66940475rel-(3S,4R)-1-Benzyl-4-(4-fluorophenyl)-N-methylpyrrolidin-3-amine

Product 1

HCID 58303155[(3S,4R)-1-Benzyl-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester

Procedure

In analogy to the procedure described for the synthesis of [(3S,4R)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester (example 265, a) the title compound was prepared from rac-[(3S,4R)-1-Benzyl-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-methyl-amine (WO2008128891) and 4-fluorophenyl chloroformate. MS m/e: 423.3 [M+H]+. This was followed by column chromatography on Chiralpak AD eluting with a gradient formed from ethanol and heptane. The product containing fractions were evaporated to yield the title compound as off-white solid. MS m/e: 423.3 [M+H]+.

Workup

  1. washeluting with a gradient
  2. customformed from ethanol and heptane
  3. additionThe product containing fractions
  4. customwere evaporated

Sources & evidence

ORD record
ord-65277ed4248644aca9e9db970d6e2850
Source dataset
uspto-grants-2016_01
Patent number
US09226916B2

Reaction notes

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