Tetrabutylammonium Fluoride → (3RS,4RS)-4-(3-bromophenyl)-piperidin-3-ol

HRID 1858550노트

반응식

HRID 1858550 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][N:11](C(OCC[Si](C)(C)C)=O)[CH2:10][CH:9]2[O:23]C(OCC[Si](C)(C)C)=O)[CH:5]=[CH:6][CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH:9]2[OH:23])[CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 539146402-trimethylsilylethyl (3RS,4RS)-4-(3-bromophenyl)-3-(2-trimethylsilyl-ethoxycarbonyloxy)-piperidine-1-carboxylate

생성물 1

HCID 22126337(3RS,4RS)-4-(3-bromophenyl)-piperidin-3-ol수율 81.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 470 mg (0.863 mmol) of 2-trimethylsilylethyl (3RS,4RS)-4-(3-bromophenyl)-3-(2-trimethylsilyl-ethoxycarbonyloxy)-piperidine-1-carboxylate in 3 ml of absolute tetrahydrofuran was treated with 2.65 ml (2.91 mmol) of tetrabutylammonium fluoride solution (1.1M in THF) and stirred at room temperature for 2.5 hours. Subsequently, the mixture was partitioned between methylene chloride and saturated sodium carbonate solution, the organic phase was dried over magnesium sulphate and finally the solvent was removed under reduced pressure. The crude product (440 mg) was purified by chromatography on silica gel with a 6.5:1:0.1 mixture of methylene chloride, MeOH and 25% ammonia as the eluent. There were obtained 180 mg (81% of theory) of (3RS,4RS)-4-(3-bromophenyl)-piperidin-3-ol as a light yellow oil. MS: 255, 257 (M)+.

후처리

  1. customSubsequently, the mixture was partitioned between methylene chloride and saturated sodium carbonate solution
  2. dry with materialthe organic phase was dried over magnesium sulphate
  3. customfinally the solvent was removed under reduced pressure
  4. customThe crude product (440 mg) was purified by chromatography on silica gel with a 6.5:1:0.1 mixture of methylene chloride, MeOH and 25% ammonia as the eluent

출처 및 근거

ORD 기록
ord-9e724c09e6044e698eff55fec8a17f35
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06150526

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