3-Furancarboxaldehyde, tetrahydro- → HCID 178424141、化合物

HRID 59775

反応式

HRID 59775 の反応式
[C:1]1([CH3:25])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][C@H:18]3[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20][CH2:19]3)[CH:13]=2)[O:8]1.[O:26]1[CH2:30][CH2:29][CH:28]([CH:31]=O)[CH2:27]1.[C:33]([BH3-])#[N:34].[Na+]>CO.C(O)(=O)C.C(=O)([O-])O.[Na+]>[O:26]1[CH2:30][CH2:29][CH:28]([CH2:31][NH:24][C@H:21]2[CH2:20][CH2:19][C@H:18]([O:17][C:12]3[CH:13]=[C:14]4[C:9](=[CH:10][CH:11]=3)[O:8][CH:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[CH3:25])[CH2:16][CH2:15]4)[CH2:23][CH2:22]2)[CH2:27]1.[O:26]1[CH2:30][CH2:29][CH:28]([CH2:31][N:34]([CH2:33][CH:28]2[CH2:29][CH2:30][O:26][CH2:27]2)[C@H:21]2[CH2:22][CH2:23][C@H:18]([O:17][C:12]3[CH:13]=[C:14]4[C:9](=[CH:10][CH:11]=3)[O:8][CH:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[CH3:25])[CH2:16][CH2:15]4)[CH2:19][CH2:20]2)[CH2:27]1

参加物

8

反応物 3

HCID 1575683-Furancarboxaldehyde, tetrahydro-HCID 5003444Sodium cyanoborohydrideHCID 178424139HCID 178424139、化合物

生成物 2

HCID 178424141HCID 178424141、化合物HCID 178424142HCID 178424142、化合物

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒2 回HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of 61 mg trans-4-(2-o-tolyl-chroman-6-yloxy)-cyclohexylamine (0.18 mmol) in 3 ml methanol and 0.2 ml of acetic acid at room temperature 39 mg tetrahydrofuran-3-carboxaldehyde (0.20 mmol) in 3 ml of methanol were added, and 12 mg of sodium cyanoborohydride (0.89 mmol (0.20 mmol) were then added in one portion. Stirring at room temperature was continued for 16 h. The solution was diluted with aqueous saturated sodium hydrogencarbonate solution and the aqueous layer extracted with dichloromethane. The combined organic layers were dried with sodium sulfate and filtered, and the solvent removed under reduced pressure. The crude product was purified by RP-HPLC. 23 mg of (tetrahydrofuran-3-ylmethyl)-[trans-4-(2-o-tolyl-chroman-6-yloxy)-cyclohexyl]-amine and 19 mg of bis-(tetrahydrofuran-3-ylmethyl)-[trans-4-(2-o-tolyl-chroman-6-yloxy)-cyclohexyl]-amine were isolated.

後処理

  1. extractionthe aqueous layer extracted with dichloromethane
  2. dry with materialThe combined organic layers were dried with sodium sulfate
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customThe crude product was purified by RP-HPLC

出典と根拠

ORDレコード
ord-49890fe6d6d0441ab752901cbf80fecd
出典データセット
uspto-grants-2016_09
特許番号
US09440941B2

関連ノート

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