1-Methylethyl 2-methoxyacetate → Methyl (1S,2S)-2-aminocyclohexane-1-carboxylate

HRID 1107671Notes

Reaction equation

HRID 1107671 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[C:8]([O:10][CH3:11])=[O:9].COCC(OC(C)C)=O>CC(OC)(C)C>[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 5421921-Methylethyl 2-methoxyacetateHCID 11768827Methyl (1R,2R)-2-aminocyclohexane-1-carboxylate

Product 1

HCID 10964775Methyl (1S,2S)-2-aminocyclohexane-1-carboxylateYield 46.7%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

50 g (0.32 mol) of methyl trans-2-aminocyclohexanecarboxylate were dissolved in 200 ml of MTBE and, after addition of 0.16 mol of isopropyl methoxyacetate and 0.5 g of Novozym 435 (Novo Nordisk), shaken at room temperature for 8 h. The enzyme was filtered off and then the solvent was removed and the residue was distilled under reduced pressure. 23.5 g of methyl (1S,2S)-2-aminocyclohexanecarboxylate and 35.2 g of methyl (1R,2R)-2-(2-methoxyacetylamino) cyclohexanecarboxylate were obtained, each with an ee of 99.8%. The ee of the amine was determined after N-acylation with acetic anhydride by gas chromatography on a B-PH GC column (supplied by Astec, N.J., USA), while the N-2-methoxyacetamide was put on this column without derivatization.

Workup

  1. filtrationThe enzyme was filtered off
  2. customthe solvent was removed
  3. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-d5754a2c731c4a1ab2b3cc74f5e8a928
Source dataset
uspto-grants-2000_05
Patent number
US06063615

Reaction notes

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