Acetic Acid → HCID 67386336, compound

HRID 905960Notes

Reaction equation

HRID 905960 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][C:3]1=O.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C1(C)C=CC=CC=1.C(Cl)Cl.O>[CH2:11]([NH:18][CH:3]1[CH2:4][C:5]([CH3:9])([CH3:8])[CH2:6][CH2:7][CH:2]1[CH3:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 1135552333543-18-9

Product 1

HCID 67386336HCID 67386336, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of crude racemic 2,5,5-trimethyl-cyclohexanone (theoretically 31.7 mmol) and benzylamine (3.8 mL, 34.79 mmol) in 50 mL of toluene was stirred for 45 minutes at reflux with continuous removal of H2O. The reaction mixture was cooled to RT and evaporated. The residue was taken into 50 mL of DCM and sodium triacetoxyborohydride (8.1 g, 38.22 mmol) was added, followed by acetic acid (2 mL, 34.94 mmol). The resulting mixture was stirred at RT overnight before being diluted with DCM and washed with saturated aqueous NaHCO3. The aqueous layer was back extracted twice with DCM. The combined organic layers were dried (Na2SO4), filtered, and evaporated. The residue was purified (DCM/(DCM:MeOH:NH4OH 60:10:1] 90% DCM) to give 3.84 g of racemic benzyl-(2,5,5-trimethyl-cyclohexyl)-amine. NMR showed the presence of about 5% of the trans isomer.

Workup

  1. customevaporated
  2. additionwas added
  3. stirringThe resulting mixture was stirred at RT overnight
  4. washwashed with saturated aqueous NaHCO3
  5. extractionThe aqueous layer was back extracted twice with DCM
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified (DCM/(DCM:MeOH:NH4OH 60:10:1] 90% DCM)

Sources & evidence

ORD record
ord-2d6c3a48c133484f9983e78b971b1f14
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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