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 2406335노트

반응식

HRID 2406335 반응식
[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

참가 물질

5

반응물 3

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

생성물 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]

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-a676e96026e740419e8fdc8e89db3a52
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809361B2

반응 노트

불러오는 중…