Benzylamine → 1-benzylazetidin-3-ol

HRID 2070008Notes

Reaction equation

HRID 2070008 reaction equation
Cl[CH2:2][CH:3]1[CH2:5][O:4]1.C(=O)(O)[O-].[Na+].[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(#N)C.O>[CH2:11]([N:18]1[CH2:5][CH:3]([OH:4])[CH2:2]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 7835EpichlorohydrinHCID 516892Sodium Bicarbonate

Product 1

HCID 38013451-benzylazetidin-3-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

reacting (±)-2-(chloromethyl)oxirane, sodium bicarbonate and benzylamine in acetonitrile and water to provide 1-benzyl-3-azetidinol, reacting the 1-benzyl-3-azetidinol and (2E/Z)-2-butenedioic acid at about 35° C. to about 45° C., and isolating 1-benzyl-3-azetidinol (2E/Z)-2-butenedioate;

Sources & evidence

ORD record
ord-bfaaa8ab28404ac3be1c39c8bbc498cb
Source dataset
uspto-grants-2012_10
Patent number
US08299254B2

Reaction notes

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