Hydrochloric Acid → methyl 4-[(2R)-2-(aminomethyl)-3,4-dihydro-2H-chromen-6-yl]benzoate

HRID 432086Notes

Reaction equation

HRID 432086 reaction equation
C(OC([NH:8][CH2:9][C@H:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=3)[CH:16]=2)[O:11]1)=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][CH2:9][C@H:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:20]3[CH:21]=[CH:22][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:28][CH:29]=3)[CH:16]=2)[O:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10272130methyl 4-((2R)-2-{[(tert-butoxycarbonyl)amino]methyl}-3,4-dihydro-2H-chromen-6-yl)benzoate

Product 1

HCID 9902206methyl 4-[(2R)-2-(aminomethyl)-3,4-dihydro-2H-chromen-6-yl]benzoateYield 83.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of methyl 4-((2R)-2-{[(tert-butoxycarbonyl)amino]methyl}-3,4-dihydro-2H-chromen-6-yl) benzoate (Example 18, 0.94 g, 2.37 mmol) in 5 mL 1,4-dioxane was added 1 mL of 4M hydrochloric acid in 1,4-dioxane dropwise. The resulting solution was allowed to stir at room temperature for 16 hours, followed by concentration in vacuo. At this point, diethyl ether was added and the solid was collected to provide 587 mg of product as a white solid. m/z=298.2 [MH+].

Workup

  1. concentrationfollowed by concentration in vacuo
  2. additionAt this point, diethyl ether was added
  3. customthe solid was collected

Sources & evidence

ORD record
ord-f1f82e737a6f45cf9626497e35121660
Source dataset
uspto-grants-2003_12
Patent number
US06660752B2

Reaction notes

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