CID 16711988 → Tert-butyl 5-fluorospiro[indoline-3,3'-piperidine]-1'-carboxylate

HRID 2190028Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]3)[C:9](=O)[NH:8][C:5]2=[CH:6][CH:7]=1.COCCO[Al]OCCOC.[Na]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]3)[CH2:9][NH:8][C:5]2=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a stirred solution of tert-butyl 5-fluoro-2-oxospiro[indoline-3,3′-piperidine]-1′-carboxylate (0.80 g, 2.5 mmol) in toluene (20 mL) was added dropwise a solution of sodium bis(2-methoxyethoxy) aluminium hybrid (Red-Al) in toluene (65% w/w, 1.1 mL, 3.5 mmol) at about 70° C. under N2. The reaction mixture was stirred at about 75° C. for 3 h. After cooling, the reaction mixture was quenched with EtOAc and concentrated in vacuo. The residue was diluted with EtOAc, washed with water and brine, dried and concentrated. The residue was purified by column chromatography (hexane:EtOAc, 3:1) to give tert-butyl 5-fluorospiro[indoline-3,3′-piperidine]-1′-carboxylate (0.18 g, 24%) as an oil. LCMS (APCI+) m/z 307 [M+H]+; Rt=3.66 min.

Workup

temperatureAfter cooling
customthe reaction mixture was quenched with EtOAc
concentrationconcentrated in vacuo
additionThe residue was diluted with EtOAc
washwashed with water and brine
customdried
concentrationconcentrated
customThe residue was purified by column chromatography (hexane:EtOAc, 3:1)

Sources & evidence

ORD record: ord-be74702628c0416ba4fed80ff87e9045
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324221B2

Reaction notes

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