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

HRID 1852762Notes

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-cbfc6646d38f43399b55215b17cafd80
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962611B2

Reaction notes

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