L-Alanine → HCID 11701071, compound

HRID 2061938Notes

Reaction equation

HRID 2061938 reaction equation
N[C@H](C(O)=O)C.[CH3:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O.[CH2:15]([NH2:18])[CH:16]=[CH2:17].S([O-])([O-])(=O)=O.[Mg+2]>O.ClCCl.CO.C(N(CC)CC)C.C(O)=O>[CH2:15]([NH:18][C@@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C@@H:8]1[CH3:7])[CH:16]=[CH2:17]

Participants

9

Reactant 4

HCID 5950L-AlanineHCID 7853AllylamineHCID 114192-MethylcyclohexanoneHCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 11701071HCID 11701071, compoundYield 77%

Reagents, catalysts & solvents 4

HCID 284Formic AcidSolventHCID 962WaterSolventHCID 8471TriethylamineSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 22.5 mg (35 μmol) of the catalyst from example Ala in 3.2 ml of a mixture of formic acid and triethylamine (5:2 v/v) is added dropwise to a mixture of 676 mg (6 mmol) of 2-methylcyclohexanone, 2.74 g (48 mmol of allylamine and 100 mg of magnesium sulfate, and stirred. After 7 days at room temperature, the reaction mixture is diluted with 20 ml of water and extracted three times with 15 ml of dichloromethane. The organic phase is dried over sodium sulfate. After removal of the solvent and column chromatography (silica gel, 10:1 dichloromethane/methanol), 708 mg (77% yield) of (1R,2S)-N-allyl-(2-methylcyclohexyl)amine are obtained.

Workup

  1. extractionextracted three times with 15 ml of dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulfate

Sources & evidence

ORD record
ord-9f603af9d8a141aea5a3c38481658024
Source dataset
uspto-grants-2012_10
Patent number
US08283495B2

Reaction notes

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