Sodium borohydride → 3-Cyclopentyl-2-[4-(5-methyl-tetrazol-1-yl)-3-trifluoromethyl phenyl]-propionic acid methyl ester

HRID 1936362ノート

反応式

HRID 1936362 の反応式
[CH3:1][O:2][C:3](=[O:27])/[C:4](/[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:21]([CH3:22])=[N:20][N:19]=[N:18]2)=[C:13]([C:23]([F:26])([F:25])[F:24])[CH:12]=1)=[CH:5]/[CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:1][O:2][C:3](=[O:27])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:21]([CH3:22])=[N:20][N:19]=[N:18]2)=[C:13]([C:23]([F:25])([F:24])[F:26])[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 67486640(E)-3-cyclopentyl-2-[4-(5-methyl-tetrazol-1-yl)-3-trifluoromethyl-phenyl]-acrylic acid methyl ester

生成物 1

HCID 696909583-Cyclopentyl-2-[4-(5-methyl-tetrazol-1-yl)-3-trifluoromethyl phenyl]-propionic acid methyl ester収率 99.6%

試薬・触媒・溶媒 2

HCID 11791229Dichloronickel;hexahydrate触媒HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

A solution of nickel (II) chloride hexahydrate (102 mg, 0.428 mmol) and (E)-3-cyclopentyl-2-[4-(5-methyl-tetrazol-1-yl)-3-trifluoromethyl-phenyl]-acrylic acid methyl ester (814 mg, 2.14 mmol) in methanol (20 mL) was cooled to 0° C. and then treated with sodium borohydride (265 mg, 7 mmol) in five portions. After the addition, the black reaction mixture was stirred for 15 min at 0° C. and then allowed to warm to 25° C. where it was stirred for 15 h. The reaction mixture was concentrated in vacuo, and the residue was diluted with a 3N aqueous hydrochloric acid solution (50 mL) and ethyl acetate (75 mL). The two layers were separated. The organic layer was washed with a saturated aqueous sodium chloride solution (1×50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford racemic 3-cyclopentyl-2-[4-(5-methyl-tetrazol-1-yl)-3-trifluoromethyl-phenyl]-propionic acid methyl ester (815 mg, 99%) as a viscous oil: EI-HRMS m/e calcd for C18H21F3N4O2 (M+) 382.1617, found 382.1617.

後処理

  1. additionAfter the addition
  2. temperatureto warm to 25° C. where it
  3. stirringwas stirred for 15 h
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. additionthe residue was diluted with a 3N aqueous hydrochloric acid solution (50 mL) and ethyl acetate (75 mL)
  6. customThe two layers were separated
  7. washThe organic layer was washed with a saturated aqueous sodium chloride solution (1×50 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a0b627434b5d46709d7d412e08c383d4
出典データセット
uspto-grants-2002_05
特許番号
US06388088B1

反応ノート

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