6-Oxabicyclo[3.1.0]hexane → (+/-)-trans-2-[4-(4-Chlorobenzyl)piperidin-1-yl]-cyclopentanol

HRID 1744832

반응식

HRID 1744832 반응식
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[CH:15]12[O:20][CH:19]1[CH2:18][CH2:17][CH2:16]2>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:8][CH2:9][N:10]([C@@H:18]3[CH2:17][CH2:16][CH2:15][C@H:19]3[OH:20])[CH2:11][CH2:12]2)=[CH:13][CH:14]=1

참가 물질

4

반응물 2

HCID 92446-Oxabicyclo[3.1.0]hexaneHCID 37327804-(4-Chlorobenzyl)piperidine

생성물 1

HCID 11173903(+/-)-trans-2-[4-(4-Chlorobenzyl)piperidin-1-yl]-cyclopentanol수율 73%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Following General Procedure A, a solution of 4-(4-chlorobenzyl)-piperidine (17.86 g, 85.05 mmol) and 6-oxa-bicyclo[3.1.0]hexane (50 g, 0.6 mol) in EtOH (170 mL) was stirred at 95° C. for 40 hours, allowed to cool to room temperature, and concentrated. The residue was crystallized in hot CH2Cl2 (80 mL), the crystallization mixture was concentrated to half the volume, and kept at 0° C. overnight and filtered, and the precipitate was rinsed with cold hexanes to give the product (18.2 g, 73%) as a tan solid. The mother liquors were concentrated to half the volume, diluted with CH2Cl2 and kept at −10° C. for 1 hour, and the precipitate was rinsed with cold CH2Cl2 and hexanes to give additional product (1.8 g, 7%) as a tan solid: mp 104.1–105.5° C.; IR 3436, 2928 cm−1; 1H NMR δ 1.19–1.75 (m, 8H), 1.81–1.99 (m, 4H), 2.06 (dt, J=2.5, 11.7 Hz, 1H), 2.47 (m, 1H), 2.50 (d, J=7.0 Hz, 2H), 2.90 (m, 1H), 3.07 (m, 1H), 4.10 (m, 1H), 7.06 (m, 2H), 7.23 (m, 2H); 13C NMR δ 21.63, 27.35, 32.01, 32.15, 34.31, 37.87, 42.47, 50.47, 52.97, 75.15, 75.22, 128.27, 130.43, 131.55, 139.04; MS m/z 294 (M+H)+. Anal. (C17H24ClNO.0.1H2O) C, H, N.

후처리

  1. concentrationconcentrated
  2. customThe residue was crystallized in hot CH2Cl2 (80 mL)
  3. concentrationthe crystallization mixture was concentrated to half the volume
  4. filtrationfiltered
  5. washthe precipitate was rinsed with cold hexanes

출처 및 근거

ORD 기록
ord-87ec0d14313146c7aa2cb5738e9dd04e
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07019007B2

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