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3-Furancarboxaldehyde, tetrahydro- → HCID 178424141, compound

HRID 59775
Notes
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Reaction equation

HRID 59775 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

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

Product 2

HCID 178424141HCID 178424141, compoundHCID 178424142HCID 178424142, compound

Reagents, catalysts & solvents 3

HCID 176
Acetic Acid
Solvent
HCID 887MethanolSolvent2×
HCID 516892Sodium BicarbonateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-49890fe6d6d0441ab752901cbf80fecd
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09440941B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes