ChemicalBook CAS DataBase List (S)-1-(TERT-BUTOXYCARBONYL)PIPERIDIN-3-YL METHANESULFONATE

(S)-1-(TERT-BUTOXYCARBONYL)PIPERIDIN-3-YL METHANESULFONATE synthesis

9synthesis methods

Product Name:(S)-1-(TERT-BUTOXYCARBONYL)PIPERIDIN-3-YL METHANESULFONATE
CAS Number:940890-90-4
Molecular formula:C11H21NO5S
Molecular Weight:279.35

124-63-0

143900-44-1

(S)-1-(TERT-BUTOXYCARBONYL)PIPERIDIN-3-YL METHANESULFONATE

940890-90-4

Under nitrogen protection, (S)-1-Boc-3-hydroxypiperidine (10.0 g, 49.7 mmol) and triethylamine (7.82 mL, 54.7 mmol) were dissolved in dichloromethane (60 mL) and cooled to 0 °C. Subsequently, methanesulfonyl chloride (4.23 mL, 54.7 mmol) was slowly added dropwise and the reaction mixture was stirred at this temperature for 1 hour. Upon completion of the reaction, the reaction solution was diluted with deionized water (60 mL) and filtered through a hydrophobic glass stock. The organic layer was concentrated under reduced pressure to afford tert-butyl (3S)-3-(methylsulfonyloxy)piperidine-1-carboxylate (13.9 g, 49.7 mmol, 100% yield) as a colorless solid. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ (ppm) 4.76-4.71 (m, 1H, CH), 3.69-3.66 (m, 1H), 3.65-3.60 (m, 1H), 3.49-3.43 (m, 1H), 3.37-3.31 (m, 1H), 3.07 (s, 3H, CH3) , 2.02-1.96 (m, 1H), 1.94-1.91 (m, 1H), 1.87-1.80 (m, 1H), 1.59-1.53 (m, 1H), 1.48-1.45 (m, 9H).

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143900-44-1 Synthesis

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Yield:940890-90-4 100%

Reaction Conditions:

with triethylamine in dichloromethane at 0; for 1 h;Inert atmosphere;

Steps:

1 [00224] tert-Butyl (3S)-3-methylsulfonyloxypiperidine-1-carboxylate

To a solution of (S)-1 -Boc-3-hydroxypiperidine (10.0 g, 49.7 mmol) and triethylamine (7.82 mL, 54.7 mmol in DCM (60 mL) under a nitrogen atmosphere, cooled at 0 °C, was added dropwise methanesulfonyl chloride (4.23 mL, 54.7 mmol). The mixture stirred for 1 h, diluted with water (60 mL) before being passed through a hydrophobic frit. The organic layer was concentrated under reduced pressure to afford fe/ -butyl (3S)-3-methylsulfonyloxypiperidine-1 -carboxylate (13.9 g, 49.7 mmol, 100% yield) as a colourless solid. H-NMR (400 MHz, DMSO-c/₆): δ (ppm) 4.76-4.71 (m, 1 H, CH), 3.69-3.66 (m 1 H), 3.65-3.60 (m, 1 H), 3.49-3.43 (m, 1 H), 3.37-3.31 (m, 1 H), 3.07 (s, 3H, CH₃), 2.02-1 .96 (m, 1 H), 1 .94-1 .91 (m, 1 H), 1 .87- 1 .80 (m, 1 H), 1 .59-1 .53, 1 .48-1 .45 (m, 9H)

References:

WO2014/188173,2014,A1 Location in patent:Paragraph 00224

124-63-0
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