Ammonium Chloride → 2-Cyclohexyl-2-hydroxy-2-phenylacetic Acid (3R)-1-azabicyclo[2.2.2]oct-3-yl Ester

HRID 1244462ノート

反応式

HRID 1244462 の反応式
[CH:1]1([Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:9]12[CH2:16][CH2:15][CH:12]([CH2:13][CH2:14]1)[C@@H:11]([O:17][C:18](=[O:27])[C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:10]2.[Cl-].[NH4+]>CCOCC.C1COCC1>[N:9]12[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16]1)[C@@H:11]([O:17][C:18](=[O:27])[C:19]([CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1)([OH:26])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:10]2

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 228507002-oxo-2-phenylacetic acid (3R)-1-azabicyclo[2.2.2]oct-3-yl esterHCID 178478990HCID 178478990、化合物

生成物 1

HCID 543289522-Cyclohexyl-2-hydroxy-2-phenylacetic Acid (3R)-1-azabicyclo[2.2.2]oct-3-yl Ester

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Cyclohexylmagnesium cloride, 0.127 mol (63.6 ml of a solution 2M in ether), was added to a solution of 28.7 g (0.111 mol) of 2-oxo-2-phenylacetic acid (3R)-1-azabicyclo[2.2.2]oct-3-yl ester dissolved in 350 ml of THF, at −70° C. under a N2 atmosphere. The mixture was stirred at this temperature for 10 minutes, and then warmed to room temperature. After 1 h, the reaction mixture was treated with a saturated solution of ammonium chloride and extracted twice with ethyl acetate. The organic phases were combined, washed with water, and dried over MgSO4. After removal of the solvent, the oil obtained (27.0 g) was purified by chromatography on silica gel eluting with chloroform/methanol 10:1. The yield was 18.7 g (49.2%) of a pure product, mixture of diastereomers: I-16a and I-16b.

後処理

  1. waitAfter 1 h
  2. extractionextracted twice with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customAfter removal of the solvent
  6. customthe oil obtained (27.0 g)
  7. customwas purified by chromatography on silica gel eluting with chloroform/methanol 10:1
  8. additionThe yield was 18.7 g (49.2%) of a pure product, mixture of diastereomers

出典と根拠

ORDレコード
ord-4cc93856a11b41388cb102f368686470
出典データセット
uspto-grants-2006_10
特許番号
US07122558B2

反応ノート

読み込み中…