反応 #1583876

ord-8c00b2587dd3453e8ed0bb101ea93ed9

反応方程式

COC(=O)C1=C(C)NC(C)=C(C(=O)O)[C@H]1c1cccc([N+](=O)[O-])c1
(R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid
CC1(O)CCN(CCC(c2ccccc2)c2ccccc2)C1
1-(3,3-diphenylpropyl)-3-methylpyrrolidin-3-ol
CC1(O)CCN(CCC(c2ccccc2)c2ccccc2)C1
1-(3,3-diphenylpropyl)-3-methylpyrrolidin-3-ol
[Na+].[OH-]
sodium hydroxide
C[C@]1(O)CCN(CCC(c2ccccc2)c2ccccc2)C1
(S)-1-(3,3-diphenylpropyl)-3-methylpyrrolidin-3-ol
収率 18.6%

反応条件

温度
30°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他were synthesized
  2. 2
    ろ過filtered
  3. 3
    その他to produce a white solid, which

実験手順

According to Example 15, (R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid and 1-(3,3-diphenylpropyl)-3-methylpyrrolidin-3-ol were synthesized. To a solution of D-bis(paramethylbenzoyl)tartaric acid ((+)-Di-1,4-toluoyl-D-tartaric acid) (280 g, 0.7 mol) in isopropanol (300 mL) was added a solution of 1-(3,3-diphenylpropyl)-3-methylpyrrolidin-3-ol (280 g, 0.95 mol) in isopropanol (300 mL) at 90° C. After the solution became clear, the solution was cooled down to 30° C. slowly, and filtered to produce a white solid, which was treated with sodium hydroxide to produce (S)-1-(3,3-diphenylpropyl)-3-methylpyrrolidin-3-ol (52 g) in a yield of 18.6%.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US09198902B2uspto-grants-2015_12