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Dichloromethane → (3s,5s,6s)-5-(Methoxycarbonyl)-1-methyl-6-[(4-phenyl-3,6-dihydropyridin-1(2h)-yl)carbonyl]piperidin-3-yl piperidine-1-carboxylate

HRID 61456
Notes
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Reaction equation

HRID 61456 reaction equation
[OH:1][C@@H:2]1[CH2:7][N:6]([CH3:8])[C@H:5]([C:9]([N:11]2[CH2:16][CH:15]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=[O:10])[C@@H:4]([C:23]([O:25][CH3:26])=[O:24])[CH2:3]1.C(Cl)Cl.C1N=CN([C:35]([N:37]2[CH:41]=N[CH:39]=[CH:38]2)=[O:36])C=1.N1CCC[CH2:44][CH2:43]1>>[N:37]1([C:35]([O:1][C@H:2]2[CH2:3][C@H:4]([C:23]([O:25][CH3:26])=[O:24])[C@@H:5]([C:9]([N:11]3[CH2:12][CH:13]=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH2:15][CH2:16]3)=[O:10])[N:6]([CH3:8])[CH2:7]2)=[O:36])[CH2:38][CH2:39][CH2:44][CH2:43][CH2:41]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8082PiperidineHCID 682631,1'-CarbonyldiimidazoleHCID 67304114Methyl (2s,3s,5s)-5-hydroxy-1-methyl-2-[(4-phenyl-3,6-dihydropyridin-1(2h)-yl)carbonyl]piperidine-3-carboxylate

Product 1

HCID 67304225(3s,5s,6s)-5-(Methoxycarbonyl)-1-methyl-6-[(4-phenyl-3,6-dihydropyridin-1(2h)-yl)carbonyl]piperidin-3-yl piperidine-1-carboxylate

Procedure

A solution of methyl(2S,3S,5S)-5-hydroxy-1-methyl-2-[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)carbonyl]piperidine-3-carboxylate (72 mg, 0.00020 mol) in methylene chloride (2.0 mL, 0.031 mol) was treated with N,N-carbonyldiimidazole (50 mg, 0.0003 mol) at rt for 2 h. To the mixture was added piperidine (0.060 mL, 0.00060 mol). After stirred at rt overnight, the mixture was concentrated to dry and used directly in next step.

Workup

  1. concentrationthe mixture was concentrated
  2. customto dry

Sources & evidence

ORD record
ord-9313db97b17140319bef5b7980514fb1
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09440958B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes