1-Pyrrolidinecarboxylic acid, 3-(acetylthio)-, 1,1-dimethylethyl ester, (3R)- synthesis

5synthesis methods

Product Name:1-Pyrrolidinecarboxylic acid, 3-(acetylthio)-, 1,1-dimethylethyl ester, (3R)-
CAS Number:935845-19-5
Molecular formula:C11H19NO3S
Molecular Weight:245.34

132945-75-6 Synthesis

(S)-1-Boc-3-methanesulfonyloxy-pyrrolidine

132945-75-6
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10387-40-3 Synthesis

10387-40-3
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1-Pyrrolidinecarboxylic acid, 3-(acetylthio)-, 1,1-dimethylethyl ester, (3R)-

935845-19-5
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Yield:935845-19-5 92%

Reaction Conditions:

in N,N-dimethyl-formamide at 65;

Steps:

2.2.d

[00243] To a cooled (-5 to-10°C, ice/salt bath) solution of pyrrolidinol (xiv) (18.2 g, 98 mmol) and triethylamine (28 ml, 196 mmol) in ethylacetate (150 ml) was slowly added methanesulfonyl chloride (9.1 ml, 118 mmol) via a syringe. After completion of addition, the mixture was left stirring at room temperature for one hour. Water (100 ml) was added, and the layers were separated. The organic layer was washed with 1 N aq. HCl solution (100 ml), 5% aq. sodium bicarbonate solution (100 ml), and with saturated aqueous NaCl solution (100 ml). Then, the organic layer was dried over sodium sulfate, filtered, and evaporated to dryness under reduced pressure, yielding 24.3 g (92 mmol, 94%) of a yellow oil. This oil was dissolved in 150 ml dry DMF, and potassium thioacetate (13.5 g, 119 mmol) was added. The resulting mixture was heated to 65 ⁰C overnight under a nitrogen atmosphere, the solution started to solidify after about half an hour. After the mixture was cooled to room temperature, water (250 ml) and TBME (200 ml) were added. The layers were separated, and the aqueous layer was extracted with another portion of TBME (250 ml). The combined organic layers were washed with water (3x250 ml), and with brine (200 ml), dried over sodium sulfate, filtered and evaporated to dryness under reduced pressure. Yield: 20.8 g (92%) of a yellow oil, identified as xvi by ¹H- NMR.

References:

WO2007/50522,2007,A1 Location in patent:Page/Page column 57-58

127423-61-4 Synthesis