Tetrahydrofuran → ethyl 4-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-(3-fluorophenyl)piperidin-1-yl]-4-oxobutanoate

HRID 1691706ノート

反応式

HRID 1691706 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH:13]([CH2:14][N:15]([C@@H:23]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)[CH3:24])[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:12][CH2:11][NH:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Cl[C:36](=[O:44])[CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40].C1COCC1.[Cl-].[NH4+]>C(N(CC)CC)C>[C:18]([O:17][C:16]([N:15]([CH2:14][CH:13]1[CH2:12][CH2:11][N:10]([C:36](=[O:44])[CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:9][CH:8]1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[C@@H:23]([C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1)[CH3:24])=[O:22])([CH3:19])([CH3:21])[CH3:20]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 84648Butanoic acid, 4-chloro-4-oxo-, ethyl esterHCID 59178728tert-butyl {[3-(3-fluorophenyl)piperidin-4-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate

生成物 1

HCID 66906545ethyl 4-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-(3-fluorophenyl)piperidin-1-yl]-4-oxobutanoate収率 99.7%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

To a mixture of 139 mg of tert-butyl {[3-(3-fluorophenyl)piperidin-4-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate, 54 mg of ethyl 4-chloro-4-oxobutanoate, and 4.0 mL of THF was added 0.084 mL of triethylamine at room temperature, followed by stirring for 3 days. To the reaction mixture was added a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 177 mg of ethyl 4-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-(3-fluorophenyl)piperidin-1-yl]-4-oxobutanoate as a colorless oily compound. ESI+: 591

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThen, the organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-0708891be5ba499c8e9abd6176478ee6
出典データセット
uspto-grants-2012_04
特許番号
US08153658B2

反応ノート

読み込み中…