2-Bromoanisole → 1-Boc-4-(2-methoxyphenyl)-4-hydroxypiperidine

HRID 276885노트

반응식

HRID 276885 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].CCCCCC.C([Li])CCC.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][C:31](=[O:34])[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].[Cl-].[NH4+]>O1CCCC1>[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][C:31]([OH:34])([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH3:9])[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

참가 물질

6

반응물 4

HCID 113582-BromoanisoleHCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178418244HCID 178418244, 화합물

생성물 1

HCID 226295651-Boc-4-(2-methoxyphenyl)-4-hydroxypiperidine수율 62.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

2-Bromoanisole (5.0 g, 27 mmol) was dissolved in anhydrous tetrahydrofuran (60 ml) to which, while stirring, was subsequently added dropwise n-butyl lithium hexane solution (17 ml, 27 mmol) spending 20 minutes at −78° C. in an atmosphere of argon. After additional 30 minutes of stirring, to this was added dropwise anhydrous tetrahydrofuran solution (40 ml) of 1-t-butoxycarbonyl-4-piperidone (5.3 g, 27 mmol) spending 40 minutes. After additional 3.5 hours of stirring, to this was added saturated ammonium chloride aqueous solution (200 ml). The reaction product was extracted with ethyl acetate, washed with saturated brine and dried with anhydrous sodium sulfate. Then 5.2 g of the aforementioned compound of interest (17 mmol, 63% in yield) was obtained by evaporating the solvent under a reduced pressure.

후처리

  1. stirringAfter additional 30 minutes of stirring
  2. waitspending 40 minutes
  3. stirringAfter additional 3.5 hours of stirring
  4. extractionThe reaction product was extracted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried with anhydrous sodium sulfate

출처 및 근거

ORD 기록
ord-bc63148425f84ac9ad0f273ede82b67e
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355642B1

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