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 1761460ノート

反応式

HRID 1761460 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a7cf4791d8e9437fa8cfc06e7776eace
出典データセット
uspto-grants-1989_05
特許番号
US04826857

反応ノート

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