Sodium Hydroxide → Tert-butyl 2-(1-(4-bromophenyl)piperidin-4-yloxy)acetate

HRID 57592노트

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HRID 57592 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][CH:11]([O:14][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 235052161-(4-Bromophenyl)piperidin-4-ol

생성물 1

HCID 86717376Tert-butyl 2-(1-(4-bromophenyl)piperidin-4-yloxy)acetate수율 83.2%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매

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온도
0 °C

실험 절차

Tetrabutylammonium bromide (1.06 g, 3.3 mmol) is added to a solution of 1-(4-bromophenyl)piperidin-4-ol (2.56 g, 10 mmol) in toluene (30 mL). The reaction mixture was cooled to 0° C. and aq. 35% sodium hydroxide (30 mL) was added followed by a drop-wise addition of tert-butyl bromoacetate (2.92 g, 15 mmol). The mixture was then allowed to reach room temperature and was stirred for 17 hours at this temperature. The layers were separated and the organic layer was washed twice with water (4 mL), dried over sodium sulfate, concentrated under vacuum and co-evaporated with petroleum ether. Purification of the crude material by flash column chromatography on silica gel (0-20% ethyl acetate in petroleum ether) yielded the desired pure material 3.08 g as pale yellow solid. MS (m/z): 372 (M+2)+

후처리

  1. customto reach room temperature
  2. customThe layers were separated
  3. washthe organic layer was washed twice with water (4 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum and co-evaporated with petroleum ether
  6. customPurification of the crude material by flash column chromatography on silica gel (0-20% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-e0555bf4748e40bda55444f47f18849a
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434726B2

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