85385-06-4 → N-(2',6'-dimethylphenyl)-1-methoxymethylethylamine

HRID 2211297Notes

Reaction equation

HRID 2211297 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]=[C:10]([CH2:12][O:13][CH3:14])[CH3:11].[H][H]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.ClCCl.O1CCCC1>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[NH:9][CH:10]([CH2:12][O:13][CH3:14])[CH3:11]

Participants

6

Reactant 2

HCID 1106323985385-06-4HCID 178418361HCID 178418361, compound

Product 1

HCID 10899497N-(2',6'-dimethylphenyl)-1-methoxymethylethylamine

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

The general procedure described in Example B1 is repeated, with the following modifications to the reaction conditions: A catalyst solution is prepared consisting of 5.3 mg of [Ir((1,5-cyclooctadien)Cl]2 (0.0079 mmol), 10.2 mg of A (0.017 mmol) and 11.9 mg of tetrabutylammonium iodide (0.032 mmol) in 5 ml of tetrahydrofuran/dichloromethane (1:1). A substrate solution consisting of 1.5 g of N-(2',6'-dimethylphenyl)-1-methoxymethyl-ethylideneamine (7.8 mmol) in 5 ml of tetrahydrofuran is also used. Hydrogenation is carried out with hydrogen under a pressure of 40 bar. The reaction temperature is 30° C. After 91 hours the conversion is 90%, the ee is 59% (R).

Workup

  1. customis repeated, with the following modifications to the reaction conditions
  2. customA catalyst solution is prepared
  3. customis 30° C

Sources & evidence

ORD record
ord-38c8e94982ea462f8e6fdfb1af772033
Source dataset
uspto-grants-1995_10
Patent number
US05463097

Reaction notes

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