Benzyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate → Benzyl 4-fluoromethyl-4-hydroxy-1-piperidinecarboxylate

HRID 2300148Notes

Reaction equation

[FH:1].[K].[O:3]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH2:7][CH2:6]2)[CH2:4]1>C(Cl)Cl>[F:1][CH2:4][C:5]1([OH:3])[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1

Participants

Conditions

Temperature: 120 °C

Procedure

3.2 g of potassium hydrogen fluoride and 610 mg tetra-n-butyl ammonium dihydrogen trifluoride were added to 5 g of benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate, and it was stirred at 120° C. for 7 hr. After cooling, methylene chloride was added thereto and it was filtered through Celite. The filtrate was evaporated, and the resulting residue was subjected to silica gel column chromatography to give 4.7 g of the title compound.

Workup

temperatureAfter cooling
filtrationit was filtered through Celite
customThe filtrate was evaporated

Sources & evidence

ORD record: ord-34574b9511ae4de5b3ab03f00157edeb
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498159B1

Reaction notes

Loading…