Dimethyl Sulfide → (R)-tert-butyl 3-((R)-(5-chloro-2-methylphenyl)(hydroxy)methyl)piperidine-1-carboxylate

HRID 2039913노트

반응식

HRID 2039913 반응식
S(C)C.C1(C)C=CC=CC=1.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:33])=[C:16]([CH:32]=1)[C:17]([C@@H:19]1[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20]1)=[O:18]>C1COCC1>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:33])=[C:16]([C@H:17]([OH:18])[C@@H:19]2[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[CH2:20]2)[CH:32]=1

참가 물질

5

반응물 3

HCID 1068Dimethyl SulfideHCID 1140TolueneHCID 58011514(R)-tert-butyl 3-(5-chloro-2-methylbenzoyl)piperidine-1-carboxylate

생성물 1

HCID 58011541(R)-tert-butyl 3-((R)-(5-chloro-2-methylphenyl)(hydroxy)methyl)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-15 °C

실험 절차

A mixture of 10 M BH3.Me2S in THF (25.4 mL, 0.254 mol) and 1M R-CBS-oxazaborolidine in toluene (38 mL, 0.038 mol) were dissolved in 100 mL anhydrous THF and cooled to −15° C. (R)-tert-butyl 3-(5-chloro-2-methylbenzoyl)piperidine-1-carboxylate in 200 mL anhydrous THF was added dropwise to the above solution and stirred at −15° C. for 2 hr. The reaction was quenched with methanol (300 mL). The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give (R)-tert-butyl 3-((R)-(5-chloro-2-methylphenyl)(hydroxy)methyl)piperidine-1-carboxylate (32 g), which contained 30% isomer.

후처리

  1. additionwas added dropwise to the above solution
  2. customThe reaction was quenched with methanol (300 mL)
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-7cddd1692fa6478b892f6f50195f913f
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580823B2

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