Acetic Acid → HCID 68466114, compound

HRID 2060864Notes

Reaction equation

HRID 2060864 reaction equation
CO[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6]C=[C:8]2[NH:13][CH3:14].[CH3:15][CH:16]([CH3:20])[CH2:17]C=O.[C:21](O)(=O)[CH3:22].[BH-](O[C:35]([CH3:37])=O)(OC(C)=O)OC(C)=O.[Na+].[C:39]([O-])(O)=O.[Na+].C[CH2:45][O:46][C:47]([CH3:49])=O>C(Cl)Cl>[CH3:45][O:46][C:47]1[CH:49]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH:12]=[CH:11][CH:10]=[C:9]2[CH2:8][N:13]([CH2:35][CH2:37][CH:21]([CH3:22])[CH3:39])[CH2:14][CH2:15][CH:16]([CH3:20])[CH3:17]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 115523-MethylbutanalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 123363895-Methoxy-N-methylnaphthalen-1-amine

Product 1

HCID 68466114HCID 68466114, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methoxynaphthalen-1-yl-methylamine (Preparation 12) (1.83 g, 9.80 mmol) in DCM (100 mL) was added 3-methylbutyraldehyde (1.26 mL, 11.8 mmol), acetic acid (0.6 mL, 10.5 mmol) and NaBH(OAc)3 (3.2 g, 15.1 mmol). The mixture was stirred for 48 h at rt. Following the addition of EtOAc (200 mL) and NaHCO3 solution (200 mL the mixture was stirred for 1 h. The organic phase was separated, washed with brine and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (hexane:EtOAc, 5:1) to give the title compound: RT=2.65 min; m/z (ES+)=314.5 [M+H]+.

Workup

  1. stirringwas stirred for 1 h
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customSolvent was removed in vacuo
  6. customthe residue purified by column chromatography (hexane:EtOAc, 5:1)

Sources & evidence

ORD record
ord-a512e387a4bd45a6a8b29aceb01dbbb1
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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