Tert-butyl 4-hydroxypiperidine-1-carboxylate → HCID 25001215, compound

HRID 1437280Notes

Reaction equation

COCCN(S(F)(F)[F:11])CCOC.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24](O)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([F:11])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: -78 °C

Procedure

In an argon atmosphere and while cooling at −78° C., [bis(2-methoxyethyl)amino]sulfur trifluoride (7.33 mL) was added dropwise to 4-hydroxy-1-piperidinecarboxylic acid tert-butyl ester (4.00 g) in methylene chloride (80 mL), followed by stirring for 30 minutes. The resultant mixture was stirred at 0° C. for 30 minutes and then at room temperature for 2 hours. The reaction mixture was partitioned by use of saturated aqueous sodium hydrogencarbonate and chloroform. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, and the residue was purified through silica gel column chromatography (chloroform-ethyl acetate) to thereby give 4-fluoropiperidine-N-carboxylic acid tert-butyl ester as an oily product (1.77 g, 44%).

Workup

waitat room temperature for 2 hours
customThe reaction mixture was partitioned by use of saturated aqueous sodium hydrogencarbonate and chloroform
dry with materialThe organic layer was dried over sodium sulfate anhydrate
filtrationfollowed by filtration
customThe solvent was removed under reduced pressure
customthe residue was purified through silica gel column chromatography (chloroform-ethyl acetate) to thereby give 4-fluoropiperidine-N-carboxylic acid tert-butyl ester as an oily product (1.77 g, 44%)

Sources & evidence

ORD record: ord-af4a751e213646019b9e69b5547aa50f
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622471B2

Reaction notes

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