Tert-butyl 4-(5-bromo-2-fluorobenzoyl)-4-hydroxypiperidine-1-carboxylate → tert-Butyl 5-bromo-3-oxo-3H-spiro[benzofuran-2,4'-piperidine]-1'-carboxylate

HRID 2046701Notes

Reaction equation

C(O[K])(C)(C)C.[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]([C:21](=[O:30])[C:22]2[CH:27]=[C:26]([Br:28])[CH:25]=[CH:24][C:23]=2F)([OH:20])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]2([C:21](=[O:30])[C:22]3[CH:27]=[C:26]([Br:28])[CH:25]=[CH:24][C:23]=3[O:20]2)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

Conditions

Temperature: 70 °C

Procedure

A 1 M solution of tBuOK (54.10 ml, 54.10 mmol) in THF was added to a solution of 4-(5-bromo-2-fluoro-benzoyl)-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (14.5 g, 36.07 mmol) in THF (200 ml) and the mixture was stirred at 70° C. After 30 min, the solution was poured into ice water (150 ml) and the product was extracted with AcOEt. The combined organic layers were washed with water (50 ml), brine (50 ml), dried over Na2SO4, then filtered and evaporated to give a pale yellow oil. Purification by column chromatography (hexane/AcOEt: 80/20 to AcOEt) gave 1.5 g of 5-bromo-3-oxo-spiro[benzofuran-2(3H),4′-piperidin]-1′-carboxylic acid tert-butyl ester as a yellow crystalline solid.

Workup

extractionthe product was extracted with AcOEt
washThe combined organic layers were washed with water (50 ml), brine (50 ml)
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated
customto give a pale yellow oil
customPurification by column chromatography (hexane/AcOEt: 80/20 to AcOEt)

Sources & evidence

ORD record: ord-b2f2ce8538724995bd7ee1d032da3557
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592444B2

Reaction notes

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