Triethylamine → 1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

HRID 2354025Notes

Reaction equation

C(OCC)(=O)C.[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C.[S:28](Cl)([CH3:31])(=[O:30])=[O:29]>O>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([O:20][S:28]([CH3:31])(=[O:30])=[O:29])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

Conditions

Temperature: 5 °C

Procedure

To 300 ml of an ethyl acetate solution containing 30.00 g of N-t-butoxycarbonyl-4-hydroxypiperidine and 41.6 ml of triethylamine was added dropwise 17.3 ml of mesyl chloride at −10° C. over 10 minutes. The temperature increased to 5° C. due to heat generation. After stirring with cooling in an ice bath for 10 minutes, 90 ml of water was carefully added dropwise to the reaction mixture. The temperature increased from 0° C. to 6° C. due to heat generation. After stirring for 10 minutes, the mixture was separated and the organic phase washed with water (90 ml×2), saturated saline (90 ml), water (90 ml) and saturated saline (90 ml) in this order. After drying with anhydrous magnesium sulfate, concentration was conducted under reduced pressure and 40.74 g of 1-t-butoxycarbonyl-4-mesyloxypiperidine was obtained.

Workup

temperatureto heat generation
temperaturewith cooling in an ice bath for 10 minutes
temperatureThe temperature increased from 0° C. to 6° C. due
temperatureto heat generation
stirringAfter stirring for 10 minutes
customthe mixture was separated
washthe organic phase washed with water (90 ml×2), saturated saline (90 ml), water (90 ml) and saturated saline (90 ml) in this order
dry with materialAfter drying with anhydrous magnesium sulfate, concentration

Sources & evidence

ORD record: ord-583c4432629f4a7dbd167032777513a1
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750156B2

Reaction notes

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