Water → HCID 70116552、化合物

HRID 862127ノート

反応式

HRID 862127 の反応式
[CH3:1][N:2]([CH3:27])[C:3]([C@@H:5]1[C@@H:10]2[CH2:11][CH2:12][N:7]([CH:8]([CH:14]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]2=O)[CH2:6]1)=[O:4].[CH3:28][O:29][C:30]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][C:31]=1[CH2:32][NH2:33].O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1(C)C=CC=CC=1.C(O)(=O)C>[CH3:1][N:2]([CH3:27])[C:3]([C@@H:5]1[C@@H:10]2[CH2:11][CH2:12][N:7]([C@@H:8]([CH:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C@H:9]2[NH:33][CH2:32][C:31]2[CH:34]=[C:35]([O:38][CH3:39])[CH:36]=[CH:37][C:30]=2[O:29][CH3:28])[CH2:6]1)=[O:4]

参加物

7

反応物 4

HCID 962WaterHCID 186522,5-DimethoxybenzenemethanamineHCID 5049666Sodium triacetoxyborohydrideHCID 86752071(3R*,4S*) N,N-Dimethyl-6-diphenylmethyl-5-oxo-1-azabicyclo[2.2.2]octane-3-carboxamide

生成物 1

HCID 70116552HCID 70116552、化合物収率 44%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 1140Toluene溶媒

実験手順

A mixture of 47 (3.9 g, 10 mmol), 2,5-dimethoxybenzyl amine (1.9 g, 11 mmol) camphor sulfonic acid (120 mg) in toluene (40 ml) was heated at reflux with removal of water for 8 hours and then the solvent was removed. The residue was dissolved in small amount of THF (5 ml) and this solution was added to a solution of sodium triacetoxyborohydride (5.3 g, 25 mmol) in acetic acid (100 ml) at room temperature. The mixture was stirred at room temperature for 4 hours and the solvent was removed. Water (25 ml) was added and the mixture was neutralized with sodium bicarbonate (NaHCO3) and extracted with ethyl acetate (EtOAc) three times. The combined extracts were dried over sodium sulfate (Na2SO4) and concentrated. The crude was purified by recrystallization from EtOAc to give 49 (2.4 g, 4.4 mmol, 44%)

後処理

  1. temperaturewas heated
  2. customthe solvent was removed
  3. dissolutionThe residue was dissolved in small amount of THF (5 ml)
  4. customthe solvent was removed
  5. additionWater (25 ml) was added
  6. extractionextracted with ethyl acetate (EtOAc) three times
  7. dry with materialThe combined extracts were dried over sodium sulfate (Na2SO4)
  8. concentrationconcentrated
  9. customThe crude was purified by recrystallization from EtOAc

出典と根拠

ORDレコード
ord-b36e66361c9e47ebb4e7ccc3094cf254
出典データセット
uspto-grants-1998_02
特許番号
US05716965

反応ノート

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