1-(Diphenylmethyl)-3-azetidinyl methanesulfonate Chemical Properties

Melting point:

111-112°C

Boiling point:

459.9±34.0 °C(Predicted)

Density 

1.28±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Dichloromethane, Ether, Ethyl Acetate, Methanol

form 

Solid

pka

5.67±0.10(Predicted)

color 

White

InChI

InChI=1S/C17H19NO3S/c1-22(19,20)21-16-12-18(13-16)17(14-8-4-2-5-9-14)15-10-6-3-7-11-15/h2-11,16-17H,12-13H2,1H3

InChIKey

MSVZMUILYMLJCF-UHFFFAOYSA-N

SMILES

N1(C(C2=CC=CC=C2)C2=CC=CC=C2)CC(OS(C)(=O)=O)C1

CAS DataBase Reference

33301-41-6(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

HazardClass 

IRRITANT

HS Code 

29339900

1-(Diphenylmethyl)-3-azetidinyl methanesulfonate Usage And Synthesis

Chemical Properties

White Crystalline Solid

Uses

A proline analog and proline formation inhibitor

Synthesis

Preparation procedure of 1-(Diphenylmethyl)-3-azetidinyl methanesulfonate: To a reaction flask was charged 632 g (2.64 mol) of 1-benzhydrylazetidin- 3-ol, acetonitrile (1.9 L), and triethylamine (601 g, 1.5 equiv). The mixture was cooled in an ice-acetone bath (-5 °C). Methanesulfonyl chloride (436 g, 1.20 equiv) was added via a drop funnel while keeping the reaction temperature at less than5 °C. HPLC showed reaction completion after 15 min. Water (6.3 L) was added, and the reaction mixture was stirred for 2 h at room temperature and filtered. The filter cake was rinsed with water (2 x 1 L), pulled dry under vacuum, and directly subjected to the amination reaction in the next step. Yield 100%.

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