Sodium borohydride → 4-[(3S)-3,7-dimethyl-6-octenyloxy]benzylamine

HRID 601459Notes

Reaction equation

HRID 601459 reaction equation
[BH4-].[Na+].[CH3:3][C@@H:4]([CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=1>C(O)C.[Ni](Cl)Cl>[CH3:3][C@@H:4]([CH2:16][CH2:17][CH:18]=[C:19]([CH3:20])[CH3:21])[CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][NH2:15])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 670598394-[(3S)-3,7-dimethyl-6-octenyloxy]cyanobenzene

Product 1

HCID 670597954-[(3S)-3,7-dimethyl-6-octenyloxy]benzylamineYield 71.1%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 702EthanolSolvent

Procedure

Sodium borohydride (NaBH4, 29.4 mmol) was added to a mixture of 4-[(3S)-3,7-dimethyl-6-octenyloxy]cyanobenzene (2.52 g, 9.80 mmol) and anhydrous nickel chloride (NiCl2, 9.8 mmol) in dry ethanol (20 mL). After 2 hours the reaction mixture was filtered over Celite® and the Celite® bed was rinsed with ethanol (2×10 mL). The solution was diluted with water (150 mL) and extracted with ether (3×25 mL). The combined ethereal phase was washed with water, dried over MgSO4, and the solvent was evaporated to afford an oil which was purified by column chromatography (EtOAc-hexane) to give 4-[(3S)-3,7-dimethyl-6-octenyloxy]benzylamine as a colorless oil (1.82 g, 6.97 mmol, 71.1% yield).

Workup

  1. filtrationAfter 2 hours the reaction mixture was filtered over Celite®
  2. washthe Celite® bed was rinsed with ethanol (2×10 mL)
  3. additionThe solution was diluted with water (150 mL)
  4. extractionextracted with ether (3×25 mL)
  5. washThe combined ethereal phase was washed with water
  6. dry with materialdried over MgSO4
  7. customthe solvent was evaporated
  8. customto afford an oil which
  9. customwas purified by column chromatography (EtOAc-hexane)

Sources & evidence

ORD record
ord-1f3340967eac44ce83d461fb0bbddb47
Source dataset
uspto-grants-2011_03
Patent number
US07902363B2

Reaction notes

Loading…