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

HRID 77007ノート

反応式

HRID 77007 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8078Cyclohexane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-74b3e9a6b35b420ca4eddb16d9a94bcb
出典データセット
uspto-grants-2014_09
特許番号
US08835682B2

反応ノート

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