Hydroxylamine → 1-tert-butyl 3-methyl (2S,3S,5R)-2-[4-(4-cyano-3,5-dimethylphenyl)-3,6-dihydropyridin-1(2H)-yl]carbonyl-5-hydroxypiperidine-1,3-dicarboxylate

HRID 1726706Notes

Reaction equation

HRID 1726706 reaction equation
ClC1C=C([O:8][C@@H:9]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:12]([C:22]([N:24]3[CH2:29][CH:28]=[C:27]([C:30]4[CH:35]=[C:34]([CH3:36])[C:33]([C:37]#[N:38])=[C:32]([CH3:39])[CH:31]=4)[CH2:26][CH2:25]3)=[O:23])[C@@H:11]([C:40]([O:42][CH3:43])=[O:41])[CH2:10]2)C=NC=1.NO>CO>[C:37]([C:33]1[C:34]([CH3:36])=[CH:35][C:30]([C:27]2[CH2:28][CH2:29][N:24]([C:22]([C@@H:12]3[C@@H:11]([C:40]([O:42][CH3:43])=[O:41])[CH2:10][C@@H:9]([OH:8])[CH2:14][N:13]3[C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])=[O:23])[CH2:25][CH:26]=2)=[CH:31][C:32]=1[CH3:39])#[N:38]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 866214951-tert-butyl 3-methyl (2S,3S,5S)-5-[(5-chloropyridin-3-yl)oxy]-2-[4-(4-cyano-3,5-dimethylphenyl)-3,6-dihydropyridin-1(2H)-yl]carbonylpiperidine-1,3-dicarboxylate

Product 1

HCID 866214961-tert-butyl 3-methyl (2S,3S,5R)-2-[4-(4-cyano-3,5-dimethylphenyl)-3,6-dihydropyridin-1(2H)-yl]carbonyl-5-hydroxypiperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Part 7. 1-tert-butyl 3-methyl(2S,3S,5S)-5-[(5-chloropyridin-3-yl)oxy]-2-[4-(4-cyano-3,5-dimethylphenyl)-3,6-dihydropyridin-1 (2H)-yl]carbonylpiperidine-1,3-dicarboxylate was treated with hydroxylamine solution in methanol, using procedures analogous to those for example 152, to provide the titled product. ESI MS: (M+H) 510.1.

Sources & evidence

ORD record
ord-e756872c7c0f4d019d42bae3d056138b
Source dataset
uspto-grants-2009_02
Patent number
US07491724B2

Reaction notes

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