Bromocyclopentane → 1-Cyclopentylpiperidin-4-ol

HRID 272845노트

반응식

HRID 272845 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[CH:14]1(Br)[CH2:18][CH2:17][CH2:16][CH2:15]1>CO>[CH:14]1([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)[CH2:18][CH2:17][CH2:16][CH2:15]1

참가 물질

5

반응물 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 79341Piperidin-4-ol

생성물 1

HCID 217027851-Cyclopentylpiperidin-4-ol수율 71.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

4-Hydroxypiperidine (2.08 g, 21.2 mmol), K2CO3 (5.86 g, 2 eq.), cylopentylbromide (11.51 g, 77.6 mmol, 3.7 eq.) and MeOH (20.8 ml) were refluxed together overnight. The reaction was allowed to cool to room temperature and quenched with 2M HCl solution (40 ml) and extracted with TBME (40 ml). The aqueous phase was basified to pH 14 with a 2M NaOH solution and extracted with DCM (4×50 ml). The combined organic extracts were dried over MgSO4, filtered, washed with DCM and concentrated in vacuo to give 1-cyclopentyl-4-hydroxypiperidine (2.55 g, 71%) as a pale yellow oil.

후처리

  1. customquenched with 2M HCl solution (40 ml)
  2. extractionextracted with TBME (40 ml)
  3. extractionextracted with DCM (4×50 ml)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. washwashed with DCM
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-fc9458b8f94b44a59a393f9bdb1cd505
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456164B2

반응 노트

불러오는 중…