Water → 1-(tert-Butoxycarbonyl)-4-((p-toluenesulfonyloxy)methyl)piperidine

HRID 1472743Notes

Reaction equation

[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.O>N1C=CC=CC=1>[S:22]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)([C:19]1[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=1)(=[O:24])=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (5.0 g, 23.2 mmol) in anhydrous pyridine (18.5 mL) at 0° C. under nitrogen, p-toluenesulfonyl chloride (4.87 g, 25.55 mmol) was added in one portion. The reaction was stirred at 0° C. for 100 minutes before warming to RT. After 18 hours, the reaction mixture was poured into water (100 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with aqueous hydrochloric acid (2×100 mL, 1.0 M solution), saturated sodium chloride solution, dried (magnesium sulfate), filtered, and concentrated in vacuo to yield the title compound (7.87 g, 91%).

Workup

temperaturebefore warming to RT
waitAfter 18 hours
extractionextracted with ethyl acetate (3×50 mL)
washThe combined organic extracts were washed with aqueous hydrochloric acid (2×100 mL, 1.0 M solution), saturated sodium chloride solution
dry with materialdried (magnesium sulfate)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e69c695865bd452abc73c326be51aeed
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012644B2

Reaction notes

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