4-Toluenesulfonyl chloride → (R)-3-tosyloxymethyl-1-methylpiperidine

HRID 1384974

반응식

HRID 1384974 반응식
[OH:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([CH3:9])[CH2:4]1.[S:10](Cl)([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:12])=[O:11]>ClCCl>[S:10]([O:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([CH3:9])[CH2:4]1)([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:12])=[O:11]

참가 물질

4

반응물 2

HCID 73974-Toluenesulfonyl chlorideHCID 920113(R)-(1-methylpiperidin-3-yl)methanol

생성물 1

HCID 15895222(R)-3-tosyloxymethyl-1-methylpiperidine수율 42.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of (R)-3-hydroxymethyl-1 -methylpiperidine (2.6 g, 20 mmol) in dichloromethane (70 mL) was cooled to 5° C. and tosyl chloride (3.8 g, 20 mmol) was added in portions during 15 minutes. After the addition was complete, the reaction was allowed to warm to room temperature and was stirred for 20 hours. The reaction mixture was then concentrated and the residue partitioned between 10% potassium hydroxide (50 mL) and ether (100 mL). The ether layer was removed and the aqueous phase extracted once again with ether (50 mL). The combined ether layers were dried over magnesium sulfate and concentrated to afford (R)-3-tosyloxymethyl-1 -methylpiperidine as a white solid (2.4 g, 42%), m.p. 74.5-81.0° C.

후처리

  1. additionAfter the addition
  2. concentrationThe reaction mixture was then concentrated
  3. customthe residue partitioned between 10% potassium hydroxide (50 mL) and ether (100 mL)
  4. customThe ether layer was removed
  5. extractionthe aqueous phase extracted once again with ether (50 mL)
  6. dry with materialThe combined ether layers were dried over magnesium sulfate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-109302689e704cf1a2f324624ab9d0fb
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06262078B1

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