ethyl (3R)-piperidine-3-carboxylate → ethyl (3R)-1-{[7-(methoxymethoxy)-2H-chromen-3-yl]methyl}piperidine-3-carboxylate

HRID 217472

반응식

HRID 217472 반응식
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([CH:15]=O)[CH2:11][O:12]2)=[CH:7][CH:6]=1.[NH:17]1[CH2:22][CH2:21][CH2:20][C@@H:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClC(Cl)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([CH2:15][N:17]3[CH2:22][CH2:21][CH2:20][C@@H:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:18]3)[CH2:11][O:12]2)=[CH:7][CH:6]=1

참가 물질

6

반응물 4

HCID 185582ethyl (3R)-piperidine-3-carboxylateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 584387297-(methoxymethoxy)-2H-chromene-3-carbaldehyde

생성물 1

HCID 58438698ethyl (3R)-1-{[7-(methoxymethoxy)-2H-chromen-3-yl]methyl}piperidine-3-carboxylate

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

반응 조건

온도
80 °C

실험 절차

To a solution of 7-(methoxymethoxy)-2H-chromene-3-carbaldehyde (5.00 g) and ethyl (3R)-piperidine-3-carboxylate (4.20 mL) in dichloroethane (150 mL) was added sodium triacetoxyborohydride (12.0 g), followed by stirring at 80° C. for 4 hours. The reaction liquid was cooled to room temperature and then saturated aqueous NaHCO3 was added thereto, followed by extraction with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the vehicle was evaporated. The residue was purified by silica gel column chromatography (hexane:EtOAc=4:1) to obtain ethyl (3R)-1-{[7-(methoxymethoxy)-2H-chromen-3-yl]methyl}piperidine-3-carboxylate (7.30 g) as a yellow oily substance.

후처리

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe vehicle was evaporated
  7. customThe residue was purified by silica gel column chromatography (hexane:EtOAc=4:1)

출처 및 근거

ORD 기록
ord-5af4ddab628246b4be6b910b01411837
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193378B2

연결된 노트

불러오는 중…