rel-(3R,5S)-3,5-Dimethylpiperidine → 5-[1-(4-Chlorophenoxy)-2-methylprop-2-yl]-2-(cis)-(3,5-dimethylpiperidin-1-ylmethyl)-5-methyl-tetrahydrofuran

HRID 1761460노트

반응식

HRID 1761460 반응식
Br[CH2:2][CH:3]1[CH2:7][CH2:6][C:5]([C:9]([CH3:20])([CH3:19])[CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)([CH3:8])[O:4]1.[CH3:21][C@H:22]1[CH2:27][C@@H:26]([CH3:28])[CH2:25][NH:24][CH2:23]1>CCOCC>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:9]([C:5]2([CH3:8])[O:4][CH:3]([CH2:2][N:24]3[CH2:25][C@H:26]([CH3:28])[CH2:27][C@H:22]([CH3:21])[CH2:23]3)[CH2:7][CH2:6]2)([CH3:20])[CH3:19])=[CH:13][CH:14]=1

참가 물질

4

반응물 2

HCID 641101rel-(3R,5S)-3,5-DimethylpiperidineHCID 135634662-Bromomethyl-5-[1-(4-chlorophenoxy)-2-methylprop-2-yl]-5-methyl-tetrahydrofuran

생성물 1

HCID 136030135-[1-(4-Chlorophenoxy)-2-methylprop-2-yl]-2-(cis)-(3,5-dimethylpiperidin-1-ylmethyl)-5-methyl-tetrahydrofuran수율 45%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

16 g (0.044 mole) of 2-bromomethyl-5-[1-(4-chlorophenoxy)-2-methyl-prop-2-yl]-5-methyl-tetrahydrofuran are stirred together with 11 g (0.097 mole) of cis-3,5-dimethylpiperidine at a bath temperature of 140° C. for about 14 hours. The resulting reaction mixture is taken up in ether, washed several times with water, dried over sodium sulphate and concentrated in vacuo. The oily residue is purified by column chromatography (silica gel 60/ether-petroleum ether 1:1). 7.8 g (45% of theory) of 5-[1-(4-chlorophenoxy)-2-methyl-prop-2-yl]-2-(cis)-(3,5-dimethylpiperidin-1-ylmethyl)-5-methyl-tetrahydrofuran of refractive index nD20 =1.5049 are obtained.

후처리

  1. customThe resulting reaction mixture
  2. washwashed several times with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe oily residue is purified by column chromatography (silica gel 60/ether-petroleum ether 1:1)

출처 및 근거

ORD 기록
ord-a7cf4791d8e9437fa8cfc06e7776eace
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04826857

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