Acetic Acid → HCID 90238065, compound

HRID 2202010Notes

Reaction equation

HRID 2202010 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.[O:13]1[CH2:18][CH2:17][CH:16]([NH2:19])[CH2:15][CH2:14]1.CC(O)=O.[BH3-]C#N.[Na+]>CO>[O:13]1[CH2:18][CH2:17][CH:16]([NH:19][CH2:1][C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=2)[C:6]([O:8][CH3:9])=[O:7])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 4192234-AminotetrahydropyranHCID 639145Methyl 3-formylbenzoateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 90238065HCID 90238065, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of methyl 3-formylbenzoate (492 mg, 3.0 mmol) in MeOH (10 mL) was added tetrahydro-2H-pyran-4-amine (303 mg, 3.0 mmol) and AcOH (0.05 mL). The mixture was stirred at 25° C. for 2 h. NaBH3CN (945 mg, 15.0 mmol) was added, and the resulting mixture was stirred at 25° C. for 16 h. The reaction solution was concentrated and the residue was dissolved in water and extracted with DCM. The organic layer was concentrated, and the residue was purified by prep-TLC to give the title product (500 mg, Yield 67%). LCMS (m/z): 250.1 (M+1).

Workup

  1. stirringthe resulting mixture was stirred at 25° C. for 16 h
  2. concentrationThe reaction solution was concentrated
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with DCM
  5. concentrationThe organic layer was concentrated
  6. customthe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-e0efae27f6394b29a482bc446bdb308f
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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