Sodium borohydride → HCID 69721082, compound

HRID 2307719Notes

Reaction equation

HRID 2307719 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=O)=[CH:3][CH:2]=1.[C@@H:16]1([NH2:26])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][CH2:17]1.[BH4-].[Na+]>C(O)C>[N:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH2:11][NH:26][C@@H:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18][CH2:17]2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 70580741-Aminotetralin, (S)-HCID 226082163-(4-Pyridinyloxy)benzaldehyde

Product 1

HCID 69721082HCID 69721082, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(4-Pyridinyloxy)benzaldehyde (0.85 g, 4.27 mmol), prepared according to J. Chem. Soc. Perkin Trans 2 (1987) 1867, and (1S)-1,2,3,4-tetrahydro-1-naphthalenylamine (0.63 g, 4.29 mmol) were combined in ethanol (10 mL), briefly heated and the solvent removed under reduced pressure. This process was repeated twice more. The residual oil was dissolved in ethanol (5 mL) and stirred with sodium borohydride (0.16 g, 4.23 mmol) overnight at room temperature. The reaction mixture was quenched with water (10 mL) and diluted with diethyl ether (50 mL). The diethyl ether was washed with saturated NaHCO3 solution (3×10 mL), brine (10 mL), dried over Na2SO4, filtered and the filtrate concentrated under reduced pressure to provide the title compound as a thick orange liquid (1.19 g, 85% yield).

Workup

  1. temperaturebriefly heated
  2. customthe solvent removed under reduced pressure
  3. dissolutionThe residual oil was dissolved in ethanol (5 mL)
  4. customThe reaction mixture was quenched with water (10 mL)
  5. additiondiluted with diethyl ether (50 mL)
  6. washThe diethyl ether was washed with saturated NaHCO3 solution (3×10 mL), brine (10 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-493383858d8740b492460ef595d7f273
Source dataset
uspto-grants-2004_12
Patent number
US06831193B2

Reaction notes

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