Triethylamine → 1-cyclohexyl-N-[(1S)-1-(furan-2-yl)ethyl]piperidin-4-amine

HRID 1618114ノート

反応式

HRID 1618114 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C@@H:6]([NH2:8])[CH3:7].[CH:9]1([N:15]2[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C(N(CC)CC)C.C([BH3-])#N.[Na+]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl.CO>[CH:9]1([N:15]2[CH2:20][CH2:19][CH:18]([NH:8][C@H:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[CH3:7])[CH2:17][CH2:16]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 7047669(1S)-1-(furan-2-yl)ethan-1-amineHCID 122527641-Cyclohexylpiperidin-4-one

生成物 1

HCID 671921261-cyclohexyl-N-[(1S)-1-(furan-2-yl)ethyl]piperidin-4-amine収率 52.1%

試薬・触媒・溶媒 3

HCID 24193Titanium Tetrachloride触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

(1S)-1-(Furan-2-yl)ethanamine (0.55 gr, 5 mmol) and 1-cyclohexylpiperidin-4-one (0.91 gr, 5 mmol) were dissolved in dry dichloromethane (20 mL) in the presence of triethylamine (2 mL, 15 mmol) and titanium(IV) chloride (1M in dichloromethane, 2.5 mmol, 2.5 mL). Reaction mixture was stirred under nitrogen atmosphere for 16 hours. After dilution with methanol (10 mL), sodium cyanoborohydride was added (0.95 gr, 25 mmol) and the resulting reaction mixture was stirred for 4 hours. After dilution with ethyl acetate, the organic phase was washed with 15% ammonium hydroxide and evaporated to dryness. Title compound (0.72 gr, Y=52%) was isolated by column chromatography (dichloromethane/methanol/7N ammonia in methanol 96:2:2)

後処理

  1. customReaction mixture
  2. customthe resulting reaction mixture
  3. stirringwas stirred for 4 hours
  4. washAfter dilution with ethyl acetate, the organic phase was washed with 15% ammonium hydroxide
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-687ca5b695e643df81bb412f7b85e413
出典データセット
uspto-grants-2014_07
特許番号
US08765972B2

反応ノート

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