Sodium Hydroxide → Cinacalcet

HRID 1253375ノート

反応式

HRID 1253375 の反応式
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH:11]=O)[CH:6]=[CH:7][CH:8]=1.[C:15]1([C@H:25]([NH2:27])[CH3:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>O.C(O)(=O)C.ClCCl>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][NH:27][C@@H:25]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[CH3:26])[CH:6]=[CH:7][CH:8]=1

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 112986123-(Trifluoromethyl)benzenepropanal

生成物 1

HCID 156419Cinacalcet

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 2.12 g of 3-(3-trifluoromethylphenyl)propanal synthesized in the Step 2, 2.0 ml of (R)-1-(1-naphthyl)ethylamine, 3.42 g of sodium triacetoxyborohydride, and 150 ml of dry dichloromethane was added 0.750 ml of glacial acetic acid, and the mixture was stirred at room temperature for 5 hours. After 100 ml of water had been added and the mixture had been stirred for 3 hours, 100 ml of 2M sodium hydroxide aqueous solution was added, and the resultant was separated into an aqueous layer and an organic layer. The aqueous layer was extracted with dichloromethane, and the extract was combined with the separated organic layer, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified with column chromatography (silica gel/hexane:ethyl acetate of 4:1 to 1:1) and then concentrated to afford 3.41 g of (R)—N-(3-(3-trifluoromethylphenyl)propyl)-1-(1-naphthyl)ethylamine as an oil. The compound was dissolved in 10 ml of dichloromethane, 5 ml of 4M hydrochloric acid/dioxane and 20 ml of toluene were added, and the mixture was concentrated under reduced pressure to pureness. The residue was recrystallized from 40 ml of ethanol and 200 ml of heptane to afford 1.71 g of the captioned compound.

後処理

  1. stirringthe mixture had been stirred for 3 hours
  2. customthe resultant was separated into an aqueous layer
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with column chromatography (silica gel/hexane:ethyl acetate of 4:1 to 1:1)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-771cd5fa54a14dbca2e8e7985e337b6e
出典データセット
uspto-grants-2013_06
特許番号
US08454978B2

反応ノート

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