3-Aminopyridine → 8-Benzenesulfonyl-2-pyridin-3-yl-2,8-diaza-spiro[4.5]decan-1-one

HRID 2194006Notes

Reaction equation

HRID 2194006 reaction equation
C([O:3][C:4]([C:6]1([CH2:21][CH2:22]OC)[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:8][CH2:7]1)=O)C.[Cl-].C[Al+]C.[NH2:29][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1>CCCCCCC>[C:15]1([S:12]([N:9]2[CH2:10][CH2:11][C:6]3([C:4](=[O:3])[N:29]([C:30]4[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=4)[CH2:22][CH2:21]3)[CH2:7][CH2:8]2)(=[O:13])=[O:14])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 100093-AminopyridineHCID 16686359Dimethylalumanylium chlorideHCID 667870971-Benzenesulfonyl-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 498019588-Benzenesulfonyl-2-pyridin-3-yl-2,8-diaza-spiro[4.5]decan-1-oneYield 26.3%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

This material was prepared in analogy to example 1 step D) from 1-benzenesulfonyl-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (0.2 g), dimethylaluminium chloride in heptane (0.9 molar, 1.88 ml) and 3-amino-pyridine (0.069 g) to give the desired 8-benzenesulfonyl-2-pyridin-3-yl-2,8-diaza-spiro[4.5]decan-1-one (0.055 g) as a white solid. MS (ESI): 372.13 (MH+).

Sources & evidence

ORD record
ord-cc05953edc064e688fe5b8bcdbd0cdfe
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

Loading…