Thiophene → methyl N-(2,3-dihydro-3-methyl-1H-inden-1-yl)glycine

HRID 5779

Reaction equation

HRID 5779 reaction equation
[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH2:3]1.[NH2:12][CH2:13][C:14]([O:16]C)=[O:15].S1C=CC=[CH:19]1.C([O-])=O.[Na+]>CO.[Pd]>[CH3:19][N:12]([CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:2]([CH3:1])[CH2:3]1)[CH2:13][C:14]([OH:16])=[O:15]

Participants

7

Reactant 4

HCID 8030ThiopheneHCID 69221Glycine methyl esterHCID 2595603-Methyl-indan-1-oneHCID 2723810Sodium Formate

Product 1

HCID 67861921methyl N-(2,3-dihydro-3-methyl-1H-inden-1-yl)glycineYield 54.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 21 parts of 2,3-dihydro-3-methyl-1H-inden-1-one, 25 parts of methyl 2-aminoacetate, 2 parts of a solution of thiophene in methanol 4%, 25 parts of sodium formate and 480 parts of methanol is hydrogenated in a Parr-apparatus and at 50° C. with 5 parts of palladium-on-charcoal catalyst 10%. The reaction mixture is evaporated. The residue is taken up in water and 1,1'-oxybisethane is added. The separated organic layer is extracted with a hydrochloric acid solution 10%. The aqueous layer is made alkaline and the product is extracted with 1,1'-oxybisethane. The combined extracts are dried, filtered and evaporated, yielding 19 parts (54.1%) of methyl N-(2,3-dihydro-3-methyl-1H-inden-1-yl)glycine as a residue.

Workup

  1. customThe reaction mixture is evaporated
  2. addition1,1'-oxybisethane is added
  3. extractionThe separated organic layer is extracted with a hydrochloric acid solution 10%
  4. extractionthe product is extracted with 1,1'-oxybisethane
  5. customThe combined extracts are dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e1764cad45a24269bfb95b0d00a282b2
Source dataset
uspto-grants-1993_09
Patent number
US05246915

Linked notes

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