Ethyl 4-piperidinecarboxylate → HCID 68914381, compound

HRID 732678Notes

Reaction equation

HRID 732678 reaction equation
[C:1]([N:5]1[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@@H:7]([CH2:16][N:17]([C@@H:25]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][CH:28]=2)[CH3:26])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:6]1)(=[O:4])[CH:2]=[CH2:3].[NH:37]1[CH2:47][CH2:46][CH:40]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:39][CH2:38]1>C(O)C.C(Cl)(Cl)Cl>[C:20]([O:19][C:18]([N:17]([CH2:16][C@@H:7]1[C@@H:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:9][N:5]([C:1](=[O:4])[CH2:2][CH2:3][N:37]2[CH2:47][CH2:46][CH:40]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:39][CH2:38]2)[CH2:6]1)[C@@H:25]([C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1)[CH3:26])=[O:24])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 86628545HCID 86628545, compound

Product 1

HCID 68914381HCID 68914381, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 21889567Chloroform ethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 750 mg of tert-butyl {[(3R,4S)-1-acryloyl-4-phenylpyrrolidin-3-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate and 8 ml of an ethanol:chloroform (4:1) mixed solvent was mixed with 487 mg of ethyl isonipecotate and stirred at 60° C. for 6Hours, and the reaction solution was concentrated under a reduced pressure. The thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol) to obtain 700 mg of ethyl 1-{[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]-3-oxopropyl}piperidine-4-carboxylate as a pale yellow amorphous substance. By carrying out the Boc-elimination from the thus obtained compound in the same manner as in Example 2, ethyl 1-{3-[(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]-3-oxopropyl}pyridine-4-carboxylate dihydrochloride was obtained.

Workup

  1. additionmixed solvent
  2. concentrationthe reaction solution was concentrated under a reduced pressure
  3. customThe thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-1b5e920f57574adeb81305e8d75bb5aa
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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