1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → HCID 86598899, compound

HRID 456748Notes

Reaction equation

[OH:1][C@H:2]1[C@H:7]2[C@@H:8](I)[C@H:4]([C@@H:5]([C:18]([O:20][CH3:21])=[O:19])[N:6]2[C@@H:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:11])[CH2:3]1.O.[F-:23].C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C.C(OCC)(=O)C>[F:23][C@@H:8]1[C@H:4]2[CH2:3][C@@H:2]([OH:1])[C@@H:7]1[N:6]([C@@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:11])[C@@H:5]2[C:18]([O:20][CH3:21])=[O:19]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl (1S,3S,4S,6R,7S)-6-hydroxy-7-iodo-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate (100 mg) in acetonitrile (8 mL), was added tetrabutylammonium fluoride hydrate (102 mg). The mixture was stirred at 80° C. for 30 minutes. The resulting mixture was diluted with ethyl acetate, and washed successively with water and brine. The organic layer was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with hexane and ethyl acetate (1:1) to give the target compound (59.5 mg)

Workup

washwashed successively with water and brine
dry with materialThe organic layer was dried over sodium sulfate
customevaporated in vacuo
customThe residue was chromatographed on silica gel eluting with hexane and ethyl acetate (1:1)

Sources & evidence

ORD record: ord-4481e70188af4e8bb4a06baa935fce71
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186731B2

Reaction notes

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