Benzaldehyde → 3-(Benzylamino)quinuclidine

HRID 349215

반응식

HRID 349215 반응식
Cl.Cl.[NH2:3][CH:4]1[CH:9]2[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]2)[CH2:5]1.C([O-])([O-])=O.[Na+].[Na+].[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH4-].[Na+]>CCO>[C:19]1([CH2:18][NH:3][CH:4]2[CH:9]3[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]3)[CH2:5]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

6

반응물 4

HCID 240BenzaldehydeHCID 10340Sodium CarbonateHCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 4311764Sodium borohydride

생성물 1

HCID 2615513-(Benzylamino)quinuclidine수율 76%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 3-aminoquinuclidine dihydrochloride (8.0 g, 40.0 mmol) in EtOH (100 mL) was added excess Na2CO3 and the mixture was stirred for 1 h and then filtered. To this solution was added benzaidehyde (3.2 g, 30.0 mmol) and the reaction was stirred at room temperature for 2 h and then NaBH4 (3 pellets, 0.4 g ea.) was added and the reaction was stirred overnight at room temperature. The solvent was evaporated in vacuo and the residue was partitioned between 10% Na2CO3 and EtOAc. The organic layer was separated, dried over K2CO3, filtered and the solvent was evaporated in vacuo. The residue was chromatographed on silica (92/8 CHCl3/1.0 M NH3 in MeOH) to give N-phenylmethyl-1-azabicyclo[2.2.2]octan-3-amine (4.2 g, 76%) as an intermediate, a pale yellow oil. MH+=217. 1H NMR (CDCl3) 1.4 (m, 3H), 1.7 (m, 1H), 1.9 (m, 2H), 2.45 (2m, 1H), 2.8 (m, 5H), 3.2 (m, 1H), 3.75 (d, 2H), 7.3 (m, 5H).

후처리

  1. filtrationfiltered
  2. stirringthe reaction was stirred at room temperature for 2 h
  3. stirringthe reaction was stirred overnight at room temperature
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was partitioned between 10% Na2CO3 and EtOAc
  6. customThe organic layer was separated
  7. dry with materialdried over K2CO3
  8. filtrationfiltered
  9. customthe solvent was evaporated in vacuo
  10. customThe residue was chromatographed on silica (92/8 CHCl3/1.0 M NH3 in MeOH)

출처 및 근거

ORD 기록
ord-480e3d3718e64d739c9c618bf7b020c4
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179818B2

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