Water → trans-4-Benzyl-5,5-difluorooctahydrocyclopenta[b][1,4]oxazine

HRID 81154Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[C:19](=O)[CH2:18][O:17][C@@H:16]2[CH2:21][CH2:22][C:23]([F:25])([F:24])[C@@H:15]12)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>C1COCC1>[CH2:7]([N:14]1[CH2:19][CH2:18][O:17][C@@H:16]2[CH2:21][CH2:22][C:23]([F:25])([F:24])[C@@H:15]12)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 70 °C

Procedure

LiAlH4 (176 mg, 4.63 mmol) was added to a solution of trans-4-benzyl-5,5-difluorohexahydrocyclopenta[b][1,4]oxazin-3(2H)-one (550 mg, 2.05 mmol) in THF (15 mL) at 0° C. The reaction mixture was heated at 70° C. for 2 hours and then cooled to room temperature. 5 mL of water was added slowly to quench the reaction and then the reaction was extracted with EtOAc (100 mL). The organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4, and concentrated under reduced pressure. Purification of the residue on a silica gel column (0 to 40% EtOAc/hexanes) afforded trans-4-benzyl-5,5-difluorooctahydrocyclopenta[b][1,4]oxazine. MS ESI calc'd. for C14H17F2NO [M+H]+ 254. found 254.

Workup

temperaturecooled to room temperature
customto quench
customthe reaction
extractionthe reaction was extracted with EtOAc (100 mL)
washThe organic layer was washed with brine (50 mL)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated under reduced pressure
customPurification of the residue on a silica gel column (0 to 40% EtOAc/hexanes)

Sources & evidence

ORD record: ord-bba1a09e91fe4fa39ee492d6a9e54528
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846657B2

Reaction notes

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