2-Methoxyacetamide → (1S, 2R)-1-amino-2-(2,2-dimethoxyethyl)-cyclohexane

HRID 411851Notes

Reaction equation

HRID 411851 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:8][CH:9]([O:12][CH3:13])[O:10][CH3:11].C(OC(=O)COC)(C)C.COCC(N)=O>CC(OC)(C)C>[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:8][CH:9]([O:10][CH3:11])[O:12][CH3:13]

Participants

5

Reactant 3

HCID 1400602-MethoxyacetamideHCID 5421921-Methylethyl 2-methoxyacetateHCID 54389444trans-1-Amino-2-(2,2-dimethoxyethyl)-cyclohexane

Product 1

HCID 69828425(1S, 2R)-1-amino-2-(2,2-dimethoxyethyl)-cyclohexaneYield 46.2%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A dry solution of 2.1 g (11.2 mmole) trans-1-amino-2-(2,2-dimethoxyethyl)-cyclohexane and 1.38 g (10.4 mmole) methoxy acetic acid isopropyl ester in 20 ml MTBE was mixed with 200 mg immobilized lipase Novozym® 435 and shaken for 25 hours at room temperature. After this period of time the conversion was 49.5%. The (1R, 2S)-enantiomer was acylated to the methoxy acetamide, while the (1S, 2R)-enantiomer was not acylated. After removal of the enzyme by filtration, removal of the solvent using an rotary evaporator and purification by column chromatography (silica gel, eluation starting with MTSE and finally with MTBE/methanol)970 mg of pure (1S, 2R)-1-amino-2-(2,2-dimethoxyethyl)-cyclohexane (46% yield) were obtained.

Workup

  1. waitAfter this period of time the conversion was
  2. customAfter removal of the enzyme
  3. filtrationby filtration, removal of the solvent
  4. customan rotary evaporator and purification by column chromatography (silica gel, eluation

Sources & evidence

ORD record
ord-4175f86568c342e0b7c1513b5cf4c416
Source dataset
uspto-grants-2003_05
Patent number
US06559318B1

Reaction notes

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