Water → 1''-Cyano-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]

HRID 2406336Notes

Reaction equation

HRID 2406336 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].[CH:28]([N:31](CC)C(C)C)(C)C.BrC#N.O>ClCCl>[C:28]([N:23]1[CH2:22][CH2:21][C:20]2([CH2:19][C:18]3([O:17][C:14]4=[CH:15][N:16]=[C:11]([C:8]5[CH2:9][CH2:10][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6][CH:7]=5)[CH:12]=[C:13]4[CH2:27]3)[CH2:26]2)[CH2:25][CH2:24]1)#[N:31]

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 81531DiisopropylethylamineHCID 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]

Product 1

HCID 867012031''-Cyano-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]

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 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, 0.22 g) and N,N-diisopropyl-ethylamine (0.22 mL) in dichloromethane (20 mL) is stirred at room temperature for 5 min. Bromocyanide (60 mg) is added and the solution is stirred at room temperature for 2 h. Water is added and the mixture is extracted with dichloromethane. The combined extracts are dried (Na2SO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate/methanol 5:5:0→5:4:1) to give the title compound. Mass spectrum (ESI+): m/z=415 [M+H]+.

Workup

  1. stirringthe solution is stirred at room temperature for 2 h
  2. extractionthe mixture is extracted with dichloromethane
  3. dry with materialThe combined extracts are dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate/methanol 5:5:0→5:4:1)

Sources & evidence

ORD record
ord-2bfb72f0a7ac44b7a1db5e4d3d11e677
Source dataset
uspto-grants-2014_08
Patent number
US08809361B2

Reaction notes

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