Formaldehyde → HCID 68338070, compound
Reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O.[O:17]=[C:18]1[C:27]2([CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH2:26][C:25]2[C:20](=[N:21][CH:22]=[C:23](/[CH:33]=[CH:34]/[C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:24]=2)[NH:19]1.C(OCC)(=O)C>ClCCCl.O>[CH3:1][N:30]1[CH2:29][CH2:28][C:27]2([CH2:26][C:25]3[C:20](=[N:21][CH:22]=[C:23](/[CH:33]=[CH:34]/[C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:24]=3)[NH:19][C:18]2=[O:17])[CH2:32][CH2:31]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
Sodium triacetoxyborohydride (1.2 g, 5.73 mmol) and paraformaldehyde (172 mg, 5.73 mmol) were successively added to a suspension of (E)-ethyl 3-(2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4′-piperidine]-6-yl)acrylate (904 mg, 2.87 mmol) in 1,2-dichloroethane (40 mL) at room temperature. The reaction mixture was then heated up to 70° C. and stirred for 2 hours. After cooling down to room temperature, the reaction mixture was diluted by addition of ethyl acetate (50 mL) and water (50 mL). The aqueous layer was separated and extracted with ethyl acetate (2×50 mL). The combined organic phases were washed with a saturated solution of sodium hydrogenocarbonate (3×60 mL), dried over sodium sulfate, filtered and concentrated to dryness. The title product was obtained as a white solid (862 mg, 91%).
Workup
- temperatureAfter cooling down to room temperature
- customThe aqueous layer was separated
- extractionextracted with ethyl acetate (2×50 mL)
- washThe combined organic phases were washed with a saturated solution of sodium hydrogenocarbonate (3×60 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-77901672e3bf47dcab25724cf6858337
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321769B2
Reaction notes
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