5-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine] → 5-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1''-[(R)-2,2,2-trifluoro-1-methyl-ethyloxycarbonyl]-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

HRID 2406365Notes

Reaction equation

HRID 2406365 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[CH:12]=[C:13]3[CH2:27][C:18]4([CH2:26][C:20]5([CH2:25][CH2:24][NH:23][CH2:22][CH2:21]5)[CH2:19]4)[O:17][C:14]3=[CH:15][N:16]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].[F:28][C:29]([F:46])([F:45])[C@H:30]([O:32][C:33](=O)[O:34]C1C=CC([N+]([O-])=O)=CC=1)[CH3:31]>>[CH3:1][S:2]([N:5]1[CH2:6][CH:7]=[C:8]([C:11]2[CH:12]=[C:13]3[CH2:27][C:18]4([CH2:19][C:20]5([CH2:21][CH2:22][N:23]([C:33]([O:32][C@H:30]([CH3:31])[C:29]([F:46])([F:45])[F:28])=[O:34])[CH2:24][CH2:25]5)[CH2:26]4)[O:17][C:14]3=[CH:15][N:16]=2)[CH2:9][CH2:10]1)(=[O:4])=[O:3]

Participants

3

Reactant 2

HCID 867012045-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]HCID 86704996Carbonic acid 4-nitro-phenyl ester (R)-2,2,2-trifluoro-1-methyl-ethyl ester

Product 1

HCID 721952545-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1''-[(R)-2,2,2-trifluoro-1-methyl-ethyloxycarbonyl]-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

Procedure

The title compound is prepared from 5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1′-cyclobutane-3′,4″-piperidine] (HCl salt) and (R)-carbonic acid 4-nitro-phenyl ester 2,2,2-trifluoro-1-methyl-ethyl ester following a procedure analogous to that described for Example 12. LC (method 6): tR=1.00 min; Mass spectrum (ESI+): m/z=530 [M+H]+.

Sources & evidence

ORD record
ord-425e2ad279584dd9a83089e2f18696c3
Source dataset
uspto-grants-2014_08
Patent number
US08809361B2

Reaction notes

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