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Triethylamine → trans(+/-)-1-(Diphenylmethyl)-2-ethylazetidin-3-yl methanesulfonate

HRID 43914
Notes
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Reaction equation

HRID 43914 reaction equation
C(N(CC)CC)C.[C:8]1([CH:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:15]2[CH2:18][C@@H:17]([OH:19])[C@@H:16]2[CH2:20][CH3:21])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl.C(OCC)(=O)C>[CH3:28][S:29]([O:19][C@@H:17]1[CH2:18][N:15]([CH:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@H:16]1[CH2:20][CH3:21])(=[O:31])=[O:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86648812trans(+/-)-1-(Diphenylmethyl)-2-ethylazetidin-3-ol

Product 1

HCID 86648814trans(+/-)-1-(Diphenylmethyl)-2-ethylazetidin-3-yl methanesulfonateYield 90.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×
HCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (0.94 mL, 6.74 mmol) was added to a solution of trans(±)-1-(Diphenylmethyl)-2-ethylazetidin-3-ol obtained in Example (234b) (1.20 g, 4.49 mmol) in dichloromethane (8 mL). Then, a solution of methanesulfonyl chloride (0.45 mL, 5.83 mmol) in dichloromethane (1.5 mL) was added dropwise at room temperature, followed by stirring for four hours. The reaction solution was diluted with ethyl acetate, washed with water and brine, and then dried over anhydrous magnesium sulfate. Following filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1) to obtain 1.41 g of the title compound as a pale yellow oily substance (91%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-0a3c6780d25c413b89cc03f2fcab2449
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536197B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes