Methanol → (2S,3S)-6-Methoxy-1,3,3-trimethyl-5-[(2-phenyl-piperidin-3-ylamino)-methyl]-1,3-dihydro-indol-2-one

HRID 1243996

反応式

HRID 1243996 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:15])([CH3:14])[C:8](=[O:13])[N:9]2[CH3:12])=[CH:5][C:4]=1[CH:16]=O.[C:18]1([C@H:24]2[C@@H:29]([NH2:30])[CH2:28][CH2:27][CH2:26][NH:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CO.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:14])([CH3:15])[C:8](=[O:13])[N:9]2[CH3:12])=[CH:5][C:4]=1[CH2:16][NH:30][C@H:29]1[CH2:28][CH2:27][CH2:26][NH:25][C@H:24]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

7

反応物 4

HCID 887MethanolHCID 5049666Sodium triacetoxyborohydrideHCID 9812908(2S,3S)-2-phenylpiperidin-3-amineHCID 219318736-Methoxy-1,3,3-trimethyl-2-oxo-2,3-dihydro-1H-indole-5-carbaldehyde

生成物 1

HCID 9800738(2S,3S)-6-Methoxy-1,3,3-trimethyl-5-[(2-phenyl-piperidin-3-ylamino)-methyl]-1,3-dihydro-indol-2-one収率 81%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

To 6-Methoxy-1,3,3-trimethyl-2-oxo-2,3-dihydro-1H-indole-5-carbaldehyde (936 mg, 4.0 mmol) in 50 mL of toluene was added (2S,3S)-2-Phenyl-piperidin-3-ylamine (1.0 g, 4.0 mmol) and 3 mL of methanol. The solution was heated to reflux with azeotropic water removal for 48 h. The solution was then concentrated and the residue was dissolved in CH2Cl2. Sodiumtriacetoxyborohydride (1.0 g, 4.7 mmol) was added and the mixture was stirred overnight. The mixture was then quenched with satd NaHCO3 and the layers were separated. The aqueous portion was extracted with CH2Cl2 (2×20 mL). The combined organic portions were washed successively with brine and water and concentrated. Silica gel chromatography (10:1 EtOAc/MeOH) gave 1.27 g (81%) of the title compound as an orange oil. Treatment of the oil with ethereal HCl gave 1.44 g of the dihydrochloride salt as an off-white solid.

後処理

  1. temperatureThe solution was heated
  2. concentrationThe solution was then concentrated
  3. dissolutionthe residue was dissolved in CH2Cl2
  4. customThe mixture was then quenched with satd NaHCO3
  5. customthe layers were separated
  6. extractionThe aqueous portion was extracted with CH2Cl2 (2×20 mL)
  7. washThe combined organic portions were washed successively with brine and water
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-714f66be583b4f4cb35f212549d67f89
出典データセット
uspto-grants-2006_10
特許番号
US07119207B2

関連ノート

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