Water → 1-{2-[2-(2-Oxopiperidin-1-yl)phenyl]ethyl}azetidin-3-yl methanesulfonate

HRID 2178533노트

반응식

HRID 2178533 반응식
[OH:1][CH:2]1[CH2:5][N:4]([CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]2=[O:20])[CH2:3]1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].O>ClCCl>[CH3:28][S:29]([O:1][CH:2]1[CH2:5][N:4]([CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]2=[O:20])[CH2:3]1)(=[O:31])=[O:30]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471Triethylamine2회HCID 31297Methanesulfonyl chloride2회HCID 895006261-[2-[2-(3-Hydroxy-1-azetidinyl)ethyl]phenyl]-2-piperidinone

생성물 1

HCID 895005501-{2-[2-(2-Oxopiperidin-1-yl)phenyl]ethyl}azetidin-3-yl methanesulfonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 1-{2-[2-(3-hydroxyazetidin-1-yl)ethyl]phenyl}piperidin-2-one a11-1 (212 mg, 0.77 mmol, 1 eq) in dichloromethane (15 ml) under nitrogen is added triethylamine (216.04 μl, 1.55 mmol, 2 eq). Methanesulfonyl chloride (106.53 mg, 0.93 mmol, 1.2 eq) is added at 0° C. and the reaction mixture is allowed to reach room temperature while stirring for 2 hours under a nitrogen atmosphere. Additional triethylamine (216 μl, 1.55 mmol, 2 eq) and methanesulfonyl chloride (106.53 mg, 0.93 mmol, 1.2 eq) are added, and the reaction mixture stirred at room temperature under nitrogen for an additional hour. Water (50 ml) is then added, the two phases vigorously shaken and separated. The organic phase is dried over MgSO4, filtered and evaporated to dryness to give 1-{2-[2-(2-oxopiperidin-1-yl)phenyl]ethyl}azetidin-3-yl methanesulfonate a11-2 which is used in next step without any further purification.

후처리

  1. customto reach room temperature
  2. stirringthe reaction mixture stirred at room temperature under nitrogen for an additional hour
  3. stirringthe two phases vigorously shaken
  4. customseparated
  5. dry with materialThe organic phase is dried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-a1ce47ee271642bc8d34124759ed85f9
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067930B2

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