Diisopropylethylamine → [1-(4-Chloro-phenyl)-cyclopentyl]-(3-hydroxymethyl-piperidin-1-yl)-methanone

HRID 586390

反応式

HRID 586390 の反応式
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:21](O)=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1.C(N(C(C)C)CC)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2([C:21]([N:1]3[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]3)=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:14][CH:15]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 974471-(4-Chlorophenyl)cyclopentanecarboxylic acidHCID 107308Piperidin-3-ylmethanolHCID 2733179PyBroP

生成物 1

HCID 22335026[1-(4-Chloro-phenyl)-cyclopentyl]-(3-hydroxymethyl-piperidin-1-yl)-methanone収率 156.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of piperdin-3-yl methanol (0.342 g, 2.97 mmol), 1-(4-chloro-phenyl)-cyclopentylcarboxylic acid (1.0 g, 4.45 mmol), diisopropylethyl amine (1.9, 15.00 mmol) in dichloromethane (7 mL) was stirred at room temperature. PyBroP (2.07 g, 4.45 mmol) was added and the reaction mixture continued stirring at room temperature. After 12 h the reaction mixture was quenched with 10% KOH. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to yield a crude oil. The crude material was purified using silica gel chromatography (95:5 hexane:ethyl acetate) to yield the desired compound (1.50 g). C18H24ClNO2, LRMS (m/z)=322 (MH+).

後処理

  1. customAfter 12 h the reaction mixture was quenched with 10% KOH
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated
  5. customto yield a crude oil
  6. customThe crude material was purified

出典と根拠

ORDレコード
ord-6d88a0408e9e45d18749d05750c1b0b1
出典データセット
uspto-grants-2005_08
特許番号
US06936614B2

関連ノート

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