Diisopropylamine → HCID 59326820, compound

HRID 410269Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[C:13]([N:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1)(=[O:15])[CH3:14].C1C=CC(N[S:30]([C:33]([F:36])([F:35])[F:34])(=[O:32])=[O:31])=CC=1>C1COCC1>[F:34][C:33]([F:36])([F:35])[S:30]([O:22][C:19]1[CH2:18][CH2:17][N:16]([C:13](=[O:15])[CH3:14])[CH2:21][CH:20]=1)(=[O:32])=[O:31]

Participants

Conditions

Temperature: -78 °C

Procedure

Diisopropylamine (18.0 mL, 128 mmol) was taken up in 50 mL of THF and chilled to −78° C. Butyllithium, 2.5 M in hexanes (51.0 mL, 128 mmol) was added dropwise. After 10 min, 1-acetylpiperidin-4-one (15.0 g, 106 mmol) was added in 60 mL of THF with rigorous stirring. After 30 min, n-phenyltriflamide (41.8 g, 117 mmol) was added in 120 mL of THF. The reaction mixture was stirred at −78° C. to RT for 16 h. The reaction mixture was quenched by saturated NaHCO3, followed by extraction with EtOAc and 5% citric acid. The organic layer was washed with 1 N NaOH (2×), water (2×), and brine, then dried over MgSO4. Filtration and concentration under reduced pressure, followed by flash chromatography on silica gel (0% to 60% EtOAc/hexanes) afforded 1-acetyl-1,2,3,6-tetrahydropyridin-4-yl trifluoromethanesulfonate as a yellow oil.

Workup

waitAfter 30 min
customThe reaction mixture was quenched by saturated NaHCO3
extractionfollowed by extraction with EtOAc and 5% citric acid
washThe organic layer was washed with 1 N NaOH (2×), water (2×), and brine
dry with materialdried over MgSO4
filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record: ord-d2d24f7722084417938bbae496918d50
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759532B2

Reaction notes

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