Water → 1-(Diphenylmethyl)azetidin-3-yl methanesulfonate

HRID 633936Notes

Reaction equation

HRID 633936 reaction equation
C(N(CC)CC)C.[S:8](Cl)([CH3:11])(=[O:10])=[O:9].[CH:13]([N:26]1[CH2:29][CH:28]([OH:30])[CH2:27]1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>ClCCl>[CH3:11][S:8]([O:30][CH:28]1[CH2:29][N:26]([CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:27]1)(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (870 ml, 62.67 mmol) and mesyl chloride (390 μL, 50.13 mmol) were successively added to a solution of 1-benzhydrylazetan-3-ol (1.0 g, 41.78 mmol) in dichloromethane (10 mL) at room temperature. The reaction mixture was stirred for 1 hour and then diluted by addition of water (20 mL). The aqueous phase was separated and extracted with dichloromethane (2×40 mL). The combined organic phases were washed with a saturated solution of sodium chloride (40 mL), dried over sodium sulfate, filtered and concentrated to dryness. The title compound was obtained as a yellow solid (1.5 g, 100%).

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted with dichloromethane (2×40 mL)
  3. washThe combined organic phases were washed with a saturated solution of sodium chloride (40 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d37026e20da8477bb9483123703ead2c
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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