Isopropyl chloroformate → 1''-(Isopropyloxycarbonyl)-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 2406345Notes

Reaction equation

HRID 2406345 reaction equation
Cl[C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3].[CH3:8][S:9]([N:12]1[CH2:17][CH:16]=[C:15]([C:18]2[CH:19]=[C:20]3[CH2:34][C:25]4([CH2:33][C:27]5([CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)[CH2:26]4)[O:24][C:21]3=[CH:22][N:23]=2)[CH2:14][CH2:13]1)(=[O:11])=[O:10].C(N(CC)CC)C>ClCCl>[CH:5]([O:4][C:2]([N:30]1[CH2:31][CH2:32][C:27]2([CH2:26][C:25]3([O:24][C:21]4=[CH:22][N:23]=[C:18]([C:15]5[CH2:16][CH2:17][N:12]([S:9]([CH3:8])(=[O:11])=[O:10])[CH2:13][CH:14]=5)[CH:19]=[C:20]4[CH2:34]3)[CH2:33]2)[CH2:28][CH2:29]1)=[O:3])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 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 867012061''-(Isopropyloxycarbonyl)-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

Isopropyl chloroformate (1 mol/L in toluene; 0.15 mL) is added to 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; 60 mg), triethylamine (40 μL), and dichloromethane (5 mL) at room temperature. The solution is stirred for 3 h and then concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1→1:4) to give the title compound. LC (method 1): tR=1.02 min; Mass spectrum (ESI+): m/z=476 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1→1:4)

Sources & evidence

ORD record
ord-2d8b0feaeb194a4e8a415c1088feb230
Source dataset
uspto-grants-2014_08
Patent number
US08809361B2

Reaction notes

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