3-Hydroxy-3-methyl-azetidine-1-carboxylic acid tert-butyl ester synthesis
- Product Name:3-Hydroxy-3-methyl-azetidine-1-carboxylic acid tert-butyl ester
- CAS Number:1104083-23-9
- Molecular formula:C9H17NO3
- Molecular Weight:187.24
398489-26-4
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1104083-23-9
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Yield: 99%
Reaction Conditions:
Stage #1:tert-butyl 3-oxoazetidine-1-carboxylate;methylmagnesium chloride in tetrahydrofuran at 0; for 1 h;
Stage #2: with water;ammonium chloride in tetrahydrofuran
Steps:
100.1
Step 1 In a dry round-bottomed flask, 1-Boc-3-azetidinone (0.70 g, 4.1 mmol) was dissolved in THF (20 mL). The solution was cooled to 0° C. and methylmagnesium chloride (3.0 M solution in THF, 2.0 mL, 6.0 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 1 h. The reaction mixture was quenched with 10 mL saturated NH4Cl, diluted with 5 mL water and extracted with 100 mL EtOAc (2*). The combined organic layers were washed with 10 mL water and 10 mL brine then combined, dried over sodium sulfate, filtered and concentrated to afford 757 mg (99%) of 3-hydroxy-3-methyl-azetidine-1-carboxylic acid tert-butyl ester as an off-white solid.
References:
Hendricks, Robert Than;Hermann, Johannes;Kondru, Rama;Lou, Yan;Lynch, Stephen M.;Owens, Timothy D.;Soth, Michael US2011/230462, 2011, A1 Location in patent:Page/Page column 91
398489-26-4
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75-16-1
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1104083-23-9
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141699-55-0
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1104083-23-9
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24424-99-5
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1104083-23-9
83 suppliers
$45.00/50mg