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 61456Notes

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

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 8082Piperidine

HCID 682631,1'-Carbonyldiimidazole

HCID 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

concentrationthe mixture was concentrated
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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