Pyrrolidine, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (3S)- synthesis
- Product Name:Pyrrolidine, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (3S)-
- CAS Number:207113-36-8
- Molecular formula:C10H23NOSi
- Molecular Weight:201.38
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Yield:207113-36-8 576 mg
Reaction Conditions:
with 1H-imidazole in dichloromethane at 0; for 20 h;Inert atmosphere;
Steps:
174.1
[00552] Step 1 : To a mixture of (S)-pyrrolidin-3-ol (494 mg, 5.69 mmol) in DCM (15 mL) was added imidazole (772 mg, 1 1.37 mmol) and TBSC1 (1.03 g, 6.81 mmol), cooled to 0 °C under N2 atmosphehe. The resulting mixture was stirred for overnight at room temperature. The mixture was partitioned between NaHC03 (sat. 50 mL) and DCM (50 mL). The aqueous phase was extracted with DCM (50 mL x 2). The combied organic layer was washed with water (100 mL x2), dried over Na2S04 and concentrated to give (S)-3-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidine (576 mg, crude) as a yellow oil. lH NMR (400 MHz, CDC13): 4.30-4.27 (m, 1H), 3.08-3.02 (m, 1H), 2.80-2.74 (m, 3H), 1.84-1.77 (m, 1H), 1.64-1.59 (m, 1H), 0.82 (s, 9H), 0.00 (s, 6H),
References:
WO2015/200534,2015,A2 Location in patent:Paragraph 00552
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207113-36-8
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