5-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1''-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine] → 5-(1-Methanesulfonyl-piperidin-4-yl)-1''-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

HRID 2406354Notes

Reaction equation

HRID 2406354 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[CH:12]=[C:13]3[CH2:34][C:18]4([CH2:33][C:20]5([CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[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]>[Pd].CO>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:12]=[C:13]3[CH2:34][C:18]4([CH2:33][C:20]5([CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH2:24][CH2:25]5)[CH2:19]4)[O:17][C:14]3=[CH:15][N:16]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

4

Reactant 1

HCID 721948505-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1''-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

Product 1

HCID 867012135-(1-Methanesulfonyl-piperidin-4-yl)-1''-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A flask charged with 5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1″-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1′-cyclobutane-3′,4″-piperidine] (50 mg), 10% palladium on carbon (5 mg), and methanol (5 mL) is shaken under H2 atmosphere (1 bar) at room temperature for 2 h. The catalyst is separated by filtration and the filtrate is concentrated to give the title compound. LC (method 3): tR=0.93 min; Mass spectrum (ESI+): m/z=492 [M+H]+.

Workup

  1. customThe catalyst is separated by filtration
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-e4853f5b31ef49ae8ff773455b15a51b
Source dataset
uspto-grants-2014_08
Patent number
US08809361B2

Reaction notes

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