Dichloromethane → HCID 66739425, compound

HRID 1641378Notes

Reaction equation

HRID 1641378 reaction equation
[NH2:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1[CH3:11].COCC(OC)=O.[Cl:19]CCl>COC(C)(C)C>[ClH:19].[NH2:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1[CH3:11]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 80507Methyl methoxyacetateHCID 51899506HCID 51899506, compound

Product 1

HCID 66739425HCID 66739425, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Novozym 435 (Aldrich Corp., 1.0 g) was added to a mixture of trans-1-amino-2-methylindane (6.6 g, 0.0448) and methyl 2-methoxyacetate (5.04 g 0.0484 mol) in tert-butyl methyl ether. The mixture was heated at reflux for 2 hours, a further amount of Novozym 435 (0.5 g) added and heating is continued for an additional 2 hours. Dichloromethane was added to the cooled mixture and the biocatalyst filtered off. The organic layer was dried (sodium sulfate), evaporated and the residue dissolved in the minimum of dichloromethane. A solution of ethanolic hydrochloric acid (8N) was added and the solid filtered to give (1S,2R)-1-amino-2-methylindane hydrochloride, and the filtrate evaporated to give N-[(1R,2S)-2-methyl-1-indanyl]-2-methoxyacetamide (5.9 g), m.p. 78-79° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperatureheating
  4. filtrationthe biocatalyst filtered off
  5. dry with materialThe organic layer was dried (sodium sulfate)
  6. customevaporated
  7. dissolutionthe residue dissolved in the minimum of dichloromethane
  8. additionA solution of ethanolic hydrochloric acid (8N) was added
  9. filtrationthe solid filtered

Sources & evidence

ORD record
ord-a63d6d786a424cf0b9db0f9b90fda7b4
Source dataset
uspto-grants-2012_02
Patent number
US08114991B2

Reaction notes

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