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3-METHYL-3-AZETIDINOL synthesis

3synthesis methods
1104083-23-9 Synthesis
3-Hydroxy-3-methyl-azetidine-1-carboxylic acid tert-butyl ester

1104083-23-9
83 suppliers
$45.00/50mg

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Yield:-

Reaction Conditions:

Stage #1:tert-butyl 3-hydroxy-3-methylazetidine-1-carboxylate with trifluoroacetic acid in dichloromethane at 20; for 3 h;
Stage #2: with ammonia in methanol

Steps:

71
Description 71; 3-Methyl-3-azetidinol (D71)1 ,1-Dimethylethyl 3-hydroxy-3-methyl-1-azetidinecarboxylate (D70, 3.23 g, 17.25 mmol) was dissolved in dichloromethane (10 ml_), treated with trifluoroacetic acid (23.92 ml_, 31 1 mmol) and stirred for 3 hours at room temperature. The solvent was removed under reduced pressure and the residue passed down an SCX column (2 x 20 g) eluting with methanol, followed by 2M ammonia in methanol. Basic fractions were combined and the solvent evaporated under reduced pressure to give the title compound as an orange oil.1 H NMR δ (DMSOd6) 1.32 (3H, s), 3.11 (2H, m, partially overlapped by water signal), 3.43 (2H, m, overlapped by water signal), 5.08 (1 H, br s).

References:

GLAXO GROUP LIMITED WO2009/80682, 2009, A1 Location in patent:Page/Page column 68-69

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