Methanol → methyl rac-(1R,2R)-1-aminoindane-2-carboxylate hydrochloride

HRID 64420Notes

Reaction equation

HRID 64420 reaction equation
C(OC([NH:8][CH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]1[C:18]([OH:20])=[O:19])=O)(C)(C)C.S(Cl)([Cl:23])=O.[CH3:25]O>>[ClH:23].[NH2:8][CH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]1[C:18]([O:20][CH3:25])=[O:19]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 207435011-[(tert-Butoxycarbonyl)amino]-2,3-dihydro-1H-indene-2-carboxylic acid

Product 1

HCID 23002662methyl rac-(1R,2R)-1-aminoindane-2-carboxylate hydrochloride

Procedure

To a suspension of 750 mg of rac-(1R,2R)-1-[(tert-butoxycarbonyl)amino]indane-2-carboxylic acid in 15 ml of methanol was added 0.40 ml of thionyl chloride, followed by stirring overnight. The solvent was evaporated to about a half amount thereof under reduced pressure, to the obtained residue was added diethyl ether, and the insoluble material was collected by filtration and dried to obtain 512 mg of methyl rac-(1R,2R)-1-aminoindane-2-carboxylate hydrochloride.

Workup

  1. customThe solvent was evaporated to about a half amount
  2. additionunder reduced pressure, to the obtained residue was added diethyl ether
  3. filtrationthe insoluble material was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-460ce756d8c747909d62ad09cb7b4b3b
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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