1,4-Dioxane hydrochloride → 2-Amino-5-hydroxyindan hydrochloride

HRID 48420Notes

Reaction equation

HRID 48420 reaction equation
C(OC([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:18])[CH:15]=2)[CH2:10]1)=O)(C)(C)C.[ClH:19].O1CCOCC1>C(O)(=O)C>[ClH:19].[NH2:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:18])[CH:15]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 22719625HCID 22719625, compound

Product 1

HCID 227196432-Amino-5-hydroxyindan hydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 2-(tert-butoxycarbonylamino)-5-hydroxyindan (130 mg, 0.50 mmol) synthesized in the above Reference Production Example 1 was added 4N hydrochloric acid-dioxane (2.3 ml) and acetic acid (6.9 ml), and the mixture was stirred at room temperature for 10 minutes. By distilling off the solvent under reduced pressure, 2-amino-5-hydroxyindan hydrochloride was obtained as a crude product. This was dissolved in ethanol (3 ml). Using triethylamine (0.14 ml, 1.0 mmol), 4-chloro-5-methylthieno[2,3-d]pyrimidine (83 mg, 0.60 mmol), a similar procedure to b) in Production Example 208 was carried out. The product obtained was purified by silica gel chromatography (methylene chloride:ethyl acetate=2:1) to obtain the title compound (17 mg, 0.057 mmol) having the following physical properties:

Workup

  1. distillationBy distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-c8714b9fb0494b6487e6a3aad6c8d699
Source dataset
uspto-grants-2004_03
Patent number
US06703421B1

Reaction notes

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