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

HRID 47312Notes

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-2cab68ccb88f441482e14ebe41b0de61
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699870B2

Reaction notes

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