Acetic Acid → (R)-Quinuclidin-3-yl 2-(4-methylbenzylamino)-2-phenylacetate

HRID 77007노트

반응식

HRID 77007 반응식
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:19])[CH:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2]2.[CH3:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.C1CCCCC1>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@@H:3]([O:9][C:10](=[O:19])[CH:11]([NH:18][CH2:20][C:21]1[CH:28]=[CH:27][C:24]([CH3:25])=[CH:23][CH:22]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2]2

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 77254-MethylbenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59401091(R)-quinuclidin-3-yl 2-amino-2-phenylacetate

생성물 1

HCID 59401115(R)-Quinuclidin-3-yl 2-(4-methylbenzylamino)-2-phenylacetate수율 54.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8078Cyclohexane용매

실험 절차

To a solution of amino-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (I76) (100 mg, 0.38 mmol) in dry THF (3.84 mL), are added 4-methylbenzaldehyde (68 mL, 0.57 mmol) and AcOH (0.5 mL, 8.73 mmol). The mixture is stirred at RT and sodium triacetoxyborohydride (163 mg, 0.77 mmol) is added. The reaction is stirred at RT for 1.5 hours then cyclohexane is added and the mixture is evaporated to dryness. The crude is purified by flash chromatography (DCM/MeOH/NH4OH=95/5/0.5) to obtain the title compound as a colorless oil (76 mg, 54% yield, mixture of diastereoisomers).

후처리

  1. stirringThe reaction is stirred at RT for 1.5 hours
  2. customthe mixture is evaporated to dryness
  3. customThe crude is purified by flash chromatography (DCM/MeOH/NH4OH=95/5/0.5)

출처 및 근거

ORD 기록
ord-74b3e9a6b35b420ca4eddb16d9a94bcb
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835682B2

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