tert-Butyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate → tert-Butyl 4-(1-hydroxy-3-methoxy-3-oxo-1-(4-pivalamidopyridin-3-yl)propan-2-yl)piperidine-1-carboxylate

HRID 2378643

Reaction equation

HRID 2378643 reaction equation
COC(=O)CC1CCN(C(OC(C)(C)C)=O)CC1.C(C1C=NC=CC=1[CH2:27][C:28]([CH3:33])([CH3:32])[C:29]([NH2:31])=[O:30])=O.[OH:34][CH:35]([C:54]1[C:55](NC(=O)C(C)(C)C)=[N:56][CH:57]=[CH:58][CH:59]=1)[CH:36]([CH:41]1[CH2:46][CH2:45][N:44]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:43][CH2:42]1)[C:37]([O:39][CH3:40])=[O:38]>>[OH:34][CH:35]([C:54]1[CH:55]=[N:56][CH:57]=[CH:58][C:59]=1[NH:31][C:29](=[O:30])[C:28]([CH3:33])([CH3:32])[CH3:27])[CH:36]([CH:41]1[CH2:42][CH2:43][N:44]([C:47]([O:49][C:50]([CH3:51])([CH3:53])[CH3:52])=[O:48])[CH2:45][CH2:46]1)[C:37]([O:39][CH3:40])=[O:38]

Participants

4

Reactant 3

HCID 1514280tert-Butyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylateHCID 59731884tert-Butyl 4-(1-hydroxy-3-methoxy-3-oxo-1-(2-pivalamidopyridin-3-yl)propan-2-yl)piperidine-1-carboxylateHCID 866047923-Formyl-4-pyridinyl-2,2-dimethylpropanamide

Product 1

HCID 59732007tert-Butyl 4-(1-hydroxy-3-methoxy-3-oxo-1-(4-pivalamidopyridin-3-yl)propan-2-yl)piperidine-1-carboxylateYield 54%

Procedure

tert-butyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate (1.33 g, 5.2 mmol) and N-(3-formyl-4-pyridinyl-2,2-dimethylpropanamide (1.0 g, 4.7 mmol) were reacted in a manner analogous to the preparation of tert-butyl 4-(1-hydroxy-3-methoxy-3-oxo-1-(2-pivalamidopyridin-3-yl)propan-2-yl)piperidine-1-carboxylate. Title compound was obtained as white foam in 54% yield. (M+H)+=464.2.

Sources & evidence

ORD record
ord-3a9b8dbcd5c84cf1b6fb84b58cd1dc73
Source dataset
uspto-grants-2008_12
Patent number
US07470679B2

Linked notes

Loading…