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

HRID 2178533Notes

Reaction equation

HRID 2178533 reaction equation
[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]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 895006261-[2-[2-(3-Hydroxy-1-azetidinyl)ethyl]phenyl]-2-piperidinone

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a1ce47ee271642bc8d34124759ed85f9
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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