Hydrochloric Acid → HCID 117045592, compound

HRID 626943Notes

Reaction equation

HRID 626943 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2([C:15]([OH:17])=[O:16])[CH:10]([CH2:11]2)[CH2:9]1)=O)(C)(C)C.[ClH:18].[CH3:19]O>O1CCOCC1>[ClH:18].[CH:10]12[CH2:11][C:12]1([C:15]([O:17][CH3:19])=[O:16])[CH2:13][CH2:14][NH:8][CH2:9]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 712648723-Azabicyclo[4.1.0]heptane-3,6-dicarboxylic acid, 3-(1,1-dimethylethyl) ester

Product 1

HCID 117045592HCID 117045592, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

3-[(tert-Butoxy)carbonyl]-3-azabicyclo[4.1.0]heptane-6-carboxylic acid (5 g, 20.72 mmol) was dissolved in MeOH (200 mL) and 4M HCl in 1,4-dioxane (25.9 mL) was added. The reaction mixture was heated at 60° C. for 4 h. The reaction mixture was cooled to room temperature, then concentrated, to afford the title compound (4.0 g, 101%) as a pale yellow solid. δH (250 MHz, CDCl3) 3.69 (s, 3H), 3.42 (br s, 1H), 2.11 (br s, 5H), 1.84 (br s, 1H), 1.62 (d, J 4.2 Hz, 1H), 1.29 (br s, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-158e5ecb20db48cebae9cb9ace7cf9ca
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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