1,4-Dioxane hydrochloride → 3,3-Difluoro-1,6-diazaspiro[3,4]octane

HRID 1912413Notes

Reaction equation

HRID 1912413 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:10]2([NH:13][CH2:12][C:11]2([F:15])[F:14])[CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1.Cl.CO>C(OCC)(=O)C>[F:14][C:11]1([F:15])[C:10]2([CH2:16][CH2:17][NH:8][CH2:9]2)[NH:13][CH2:12]1

Participants

5

Reactant 3

HCID 204431481,4-Dioxane hydrochlorideHCID 21893726Hydrochloride methanolHCID 58293289Tert-butyl 3,3-difluoro-1,6-diazaspiro[3.4]octane-6-carboxylate

Product 1

HCID 582933463,3-Difluoro-1,6-diazaspiro[3,4]octaneYield 129.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To an optically-active compound of 3,3-difluoro-1,6-diazaspiro[3,4]octane-6-carboxylic acid tert-butyl ester (211 mg) were added 4M hydrochloric acid-1,4-dioxane (2.1 ml) and 2M hydrochloric acid-methanol (2.1 ml), and the mixture was stirred at room temperature for 45 minutes. To the reaction mixture was added ethyl acetate, and the mixture was filtered to give the titled compound (163 mg).

Workup

  1. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-942dc82627814c0095355308d8c14c86
Source dataset
uspto-grants-2013_12
Patent number
US08609647B2

Reaction notes

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