Isobutylene oxide → 1''-(2-Hydroxy-2-methyl-propyl)-5-(4-methylsulfonyl-phenyl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

HRID 2406335ノート

反応式

HRID 2406335 の反応式
[CH3:1][S:2]([C:5]1[CH: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)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C([O-])([O-])=O.[K+].[K+].[CH3:34][C:35]1([O:38][CH2:37]1)[CH3:36]>CO>[OH:38][C:35]([CH3:37])([CH3:36])[CH2:34][N:23]1[CH2:22][CH2:21][C:20]2([CH2:26][C:18]3([O:17][C:14]4=[CH:15][N:16]=[C:11]([C:8]5[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=5)[CH:12]=[C:13]4[CH2:27]3)[CH2:19]2)[CH2:25][CH2:24]1

参加物

5

反応物 3

HCID 11208Isobutylene oxideHCID 11430Potassium CarbonateHCID 867012015-(4-Methylsulfonyl-phenyl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

生成物 1

HCID 867012021''-(2-Hydroxy-2-methyl-propyl)-5-(4-methylsulfonyl-phenyl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 5-(4-methylsulfonyl-phenyl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1′-cyclobutane-3′,4″-piperidine] (HCl salt; 50 mg) and K2CO3 (17 mg) in methanol (4 mL) is stirred at room temperature for 15 min prior to the addition of isobutylene oxide (20 μL). The reaction vessel is sealed and the mixture is stirred at 60° C. overnight. After cooling to room temperature, the mixture is concentrated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate/methanol 5:4:1→0:9:1) to give the title compound. LC (method 1): tR=0.71 min; Mass spectrum (ESI+): m/z=457 [M+H]+.

後処理

  1. customThe reaction vessel is sealed
  2. stirringthe mixture is stirred at 60° C. overnight
  3. temperatureAfter cooling to room temperature
  4. concentrationthe mixture is concentrated
  5. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate/methanol 5:4:1→0:9:1)

出典と根拠

ORDレコード
ord-a676e96026e740419e8fdc8e89db3a52
出典データセット
uspto-grants-2014_08
特許番号
US08809361B2

反応ノート

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