Formaldehyde → HCID 68338070, compound

HRID 83085Notes

Reaction equation

[O:1]=[C:2]1[C:11]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH2:10][C:9]2[C:4](=[N:5][CH:6]=[C:7](/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=2)[NH:3]1.[C:24](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O>ClCCCl>[CH3:24][N:14]1[CH2:13][CH2:12][C:11]2([CH2:10][C:9]3[C:4](=[N:5][CH:6]=[C:7](/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=3)[NH:3][C:2]2=[O:1])[CH2:16][CH2:15]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of (E)-ethyl 3-(2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4′-piperidine]-6-yl)acrylate (99.8 mg, 0.316 mmol) in 1,2-dichloroethane (5 mL) were added sodium triacetoxyborohydride (139 mg, 0.656 mmol) and paraformaldehyde (21 mg, 0.699 mmol). The reaction mixture was heated to 70° C. for 5 h. After cooling to room temperature, the reaction mixture was partitioned between DCM (25 mL) and water (25 mL). The aqueous layer was separated and extracted with DCM (2×20 mL). The combined organic phases were washed with saturated NaHCO3 (3×25 mL) and brine (25 mL), dried over sodium sulfate and concentrated. The crude product was used directly in the next step.

Workup

temperatureAfter cooling to room temperature
customthe reaction mixture was partitioned between DCM (25 mL) and water (25 mL)
customThe aqueous layer was separated
extractionextracted with DCM (2×20 mL)
washThe combined organic phases were washed with saturated NaHCO3 (3×25 mL) and brine (25 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-417b82e6170d4c6da7b320cd01493d18
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846711B2

Reaction notes

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