Formaldehyde → HCID 68338070, 화합물

HRID 83085노트

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HRID 83085 반응식
[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

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68338146(E)-Ethyl 3-(2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4'-piperidine]-6-yl)acrylate

생성물 1

HCID 68338070HCID 68338070, 화합물

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
70 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-417b82e6170d4c6da7b320cd01493d18
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846711B2

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