3-(4-Chlorophenoxy)benzaldehyde → HCID 69722721, compound

HRID 2307616Notes

Reaction equation

HRID 2307616 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH:10]=O)=[CH:4][CH:3]=1.[C@@H:17]1([NH2:27])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH2:10][NH:27][C@@H:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19][CH2:18]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6160153-(4-Chlorophenoxy)benzaldehydeHCID 4311764Sodium borohydrideHCID 70580741-Aminotetralin, (S)-

Product 1

HCID 69722721HCID 69722721, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(4-Chlorophenoxy)benzaldehyde (1.50 mL, 7.82 mmol, purchased from Acros Organics) in 30 mL absolute ethanol was treated with (1S)-1,2,3,4-tetrahydro-1-naphthalenylamine (1.12 mL, 7.82 mmol, purchased from Lancaster). After stirring at ambient temperature for 4 hours, the mixture was treated with NaBH4 (0.33 g, 8.60 mmol) in one portion. After stirring an additional 18 hours, the reaction mixture was concentrated under reduced pressure and the residue dissolved in diethyl ether and quenched by addition of a solution of 1N NaOH. The phases were allowed to separate and the aqueous phase was extracted with diethyl ether. The organic phases were combined, washed with water, brine, dried (Na2SO4), filtered and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 15% ethyl acetate/hexanes) to provide the title compound as a colorless oil (2.26 g, 79%). 1H NMR (300 MHz, CDCl3) δ6.85-7.37 (m, 12H), 3.75-3.95 (m, 3H), 2.65-2.9 (m, 2H), 1.4-2.1 (m, 5H); MS (ESI+) 364 (M+H)+.

Workup

  1. stirringAfter stirring an additional 18 hours
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue dissolved in diethyl ether
  4. customquenched by addition of a solution of 1N NaOH
  5. customto separate
  6. extractionthe aqueous phase was extracted with diethyl ether
  7. washwashed with water, brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated under reduced pressure
  11. customThe residue was purified by flash chromatography (silica gel, 15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-7df1a3551e774e8186b0c78fe29e912a
Source dataset
uspto-grants-2004_12
Patent number
US06831193B2

Reaction notes

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