3-Furancarboxaldehyde, tetrahydro- → HCID 178424141, 화합물

HRID 59775

반응식

HRID 59775 반응식
[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

참가 물질

8

반응물 3

HCID 1575683-Furancarboxaldehyde, tetrahydro-HCID 5003444Sodium cyanoborohydrideHCID 178424139HCID 178424139, 화합물

생성물 2

HCID 178424141HCID 178424141, 화합물HCID 178424142HCID 178424142, 화합물

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-49890fe6d6d0441ab752901cbf80fecd
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440941B2

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