Formic Acid → HCID 11651734, compound

HRID 2061937Notes

Reaction equation

HRID 2061937 reaction equation
N[C@H](C(O)=O)C.C(O)=O.C(N(CC)CC)C.[CH2:17]([N:24]=[C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27][CH:26]1[CH3:35])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCl.CCCCCC.C(OCC)(=O)C>[CH2:17]([NH:24][C@@H:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27][C@@H:26]1[CH3:35])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 5950L-AlanineHCID 8471TriethylamineHCID 67184475HCID 67184475, compound

Product 1

HCID 11651734HCID 11651734, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

3 mg (4.7 μmol) of the catalyst from example Ala are dissolved in 1 ml of a mixture of formic acid and triethylamine (5:2 v/v) and stirred for 20 min. A solution of 350 mg (1.141 mmol) of racemic N-benzyl-(2-methyl-3,4-dihydro-2H-naphth-1-ylidene)amine in 1.7 ml of dichloromethane is then added and the mixture is stirred at room temperature for 5 days. After removal of the solvent, the dissolution in 5 ml of methanol, treatment with approx. 200 mg of potassium hydroxide and admixing with 10 ml of water at room temperature, extraction is effected three times with in each case 15 ml of dichloromethane and the organic phase is dried over sodium sulfate. After removal of the solvent and column chromatography (20:1 hexane/ethyl acetate), 229 mg (65% yield) of (1S,2S)-N-benzyl-(2-methyl-1,2,3,4-tetrahydronaphth-1-yl)amine are obtained as a light yellow oil.

Workup

  1. stirringthe mixture is stirred at room temperature for 5 days
  2. customAfter removal of the solvent
  3. dissolutionthe dissolution in 5 ml of methanol
  4. extractiontreatment with approx. 200 mg of potassium hydroxide and admixing with 10 ml of water at room temperature, extraction
  5. dry with materialthe organic phase is dried over sodium sulfate

Sources & evidence

ORD record
ord-07c9df556f40497fa9ef6f04739dc8c4
Source dataset
uspto-grants-2012_10
Patent number
US08283495B2

Reaction notes

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