Benzylamine → HCID 121253854, compound

HRID 905931Notes

Reaction equation

HRID 905931 reaction equation
[CH3:1][CH:2]1[C:7](=O)[CH2:6][CH2:5][O:4][CH2:3]1.[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:9]([NH:16][C@H:7]1[CH2:6][CH2:5][O:4][CH2:3][C@H:2]1[CH3:1])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 141709263-Methyloxan-4-one

Product 1

HCID 121253854HCID 121253854, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Racemic 3-methyl-tetrahydro-pyran-4-one (1 g, 8.761 mmol) was dissolved in DCM. Benzylamine (1.5 mL, 13.75 mmol) and sodium triacetoxyborohydride (95%, 3.3 g, 14.89 mmol) were added and the resulting suspension was stirred at RT overnight. The reaction mixture was washed with saturated aqueous NaHCO3. The aqueous layer was extracted with DCM. The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated. The remaining yellow liquid was purified by SiO2 chromatography (120 g SiO2, DCM/(DCM:MeOH:NH4OH 60:10:1) 92% DCM) to give 1.8 g of racemic cis benzyl-(3-methyl-tetrahydro-pyran-4-yl)-amine as a light yellow oil (>95% yield).

Workup

  1. washThe reaction mixture was washed with saturated aqueous NaHCO3
  2. extractionThe aqueous layer was extracted with DCM
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe remaining yellow liquid was purified by SiO2 chromatography (120 g SiO2, DCM/(DCM:MeOH:NH4OH 60:10:1) 92% DCM)

Sources & evidence

ORD record
ord-eff4b6b07426482a9283ec93a378d736
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

Loading…