(Diethylamino)sulfur trifluoride → 8-Benzyl-6-fluoro-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

HRID 1848478Notes

Reaction equation

CCN(S(F)(F)[F:7])CC.[CH2:10]([N:17]1[CH2:34][CH2:33][C:20]2([C:24](=[O:25])[N:23]([C:26]3[CH2:27][O:28][C:29](=[O:32])[C:30]=3[CH3:31])[CH2:22][CH2:21]2)[CH:19](O)[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[CH2:10]([N:17]1[CH2:34][CH2:33][C:20]2([C:24](=[O:25])[N:23]([C:26]3[CH2:27][O:28][C:29](=[O:32])[C:30]=3[CH3:31])[CH2:22][CH2:21]2)[CH:19]([F:7])[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a flask charged with DCM (5 mL) and a stir bar was added DAST (0.092 mL, 0.69 mmol) at −78° C., which was followed by addition of 8-benzyl-6-hydroxy-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one (I-35, Step C) (165 mg, 0.46 mmol) in DCM. The mixture was stirred at −78° C. for 15 minutes, and then allowed to warm up to RT slowly. The reaction was quenched with aq NaHCO3 and after 3 hours at RT it was extracted with DCM, dried over sodium sulfate, and purified by MPLC with hexane and EtOAc. Two spots were collected with the desired molecule weight in the ratio of 1:4. The less polar compound, which is the minor isomer, was designated as Isomer A, and the more polar major isomer was designated as Isomer B. LCMS: m/z 359 (M+H)+.

Workup

temperatureto warm up to RT slowly
customThe reaction was quenched with aq NaHCO3 and after 3 hours at RT it
extractionwas extracted with DCM
dry with materialdried over sodium sulfate
custompurified by MPLC with hexane and EtOAc
customTwo spots were collected with the desired molecule weight in the ratio of 1:4

Sources & evidence

ORD record: ord-2c88ef597340446e870ab27e330dd130
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952166B2

Reaction notes

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