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

HRID 586390

반응식

HRID 586390 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-6d88a0408e9e45d18749d05750c1b0b1
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936614B2

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