Dichloromethane → tert-Butyl 3,6-dihydropyridine-1(2H)-carboxylate

HRID 712494Notes

Reaction equation

S(O[CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)(C1C=CC(C)=CC=1)(=O)=O.C1CCN2C(=NCCC2)CC1.C(Cl)Cl>CN(C=O)C>[N:15]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17][CH:12]=[CH:13][CH2:14]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of tert-butyl 4-(tosyloxy)piperidine-1-carboxylate (5.50 g, 15.40 mmol, 1 eq) and DBU (5.70 g, 31.00 mmol, 2 eq) in DMF (100 mL) was heated at 150° C. overnight and cooled to room temperature. To this, 100 mL of CH2Cl2 was added, and the mixture was washed with brine (20 mL×3) and water (30 mL×2). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (10:1 (v/v) PE/EtOAc) to give the title compound as pale yellow oil (2.40 g, 85.00%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 184.1 (M+1).

Workup

temperaturecooled to room temperature
washthe mixture was washed with brine (20 mL×3) and water (30 mL×2)
dry with materialThe organic phase was dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (10:1 (v/v) PE/EtOAc)

Sources & evidence

ORD record: ord-cf645deac4964ca482bc448945beba3c
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181277B2

Reaction notes

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