Acetic Acid → HCID 54395232, compound

HRID 1532396Notes

Reaction equation

HRID 1532396 reaction equation
[CH:1](=O)[C:2]1[C:3]([O:8][CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.[NH2:11][CH:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]1[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCCl.C(Cl)(Cl)Cl>[C:23]1([CH2:22][C@@H:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:20][CH2:21][C@@H:12]2[NH:11][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH3:9])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 86582-MethoxybenzaldehydeHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 21251726HCID 21251726, compound

Product 1

HCID 54395232HCID 54395232, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolvent

Procedure

2-Anisaldehyde (0.22 g, 1.60 mmol) was added to a solution of 2-amino-1-benzyltetralin 10 (0.38 g, 1.60 mmol) and acetic acid (0.096 g, 1.60 mmol) in 1,2-dichloroethane (20 mL) and sodium triacetoxyborohydride (0.51 g, 2.40 mmol) under nitrogen. The resulting suspension was stirred for 5 days and then concentrated in vacuo to provide a yellow film. Saturated aqueous potassium carbonate solution (40 mL) and chloroform (40 mL) were added to this material. The layers were separated, and the aqueous layer was extracted with chloroform. The chloroform extracts were combined, dried (Na2SO4), and concentrated to provide 0.51 g of rac-cis-1-(phenylmethyl)-N-(2-methoxyphenylmethyl)-1,2,3,4-tetrahydro-2-naphthalenamine 11 as a brown oil.

Workup

  1. concentrationconcentrated in vacuo
  2. customto provide a yellow film
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with chloroform
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7fa0a46c88674e338153f6ab87f1245f
Source dataset
uspto-grants-2001_03
Patent number
US06201025B1

Reaction notes

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