Hydrochloric Acid → Tert-butyl 4-[1-(aminomethyl)-2-methoxy-2-oxoethyl]benzoate hydrochloride

HRID 1919902Notes

Reaction equation

HRID 1919902 reaction equation
[C:1]([CH:3]([C:8]1[CH:20]=[CH:19][C:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:10][CH:9]=1)[C:4]([O:6][CH3:7])=[O:5])#[N:2].[ClH:21]>CO.[Pd]>[ClH:21].[NH2:2][CH2:1][CH:3]([C:8]1[CH:9]=[CH:10][C:11]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[CH:19][CH:20]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57611881Tert-butyl 4-(1-cyano-2-methoxy-2-oxoethyl)benzoate

Product 1

HCID 67496911Tert-butyl 4-[1-(aminomethyl)-2-methoxy-2-oxoethyl]benzoate hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-(1-cyano-2-methoxy-2-oxoethyl)benzoate (3.51 g, 12.8 mmol) in MeOH (120 mL) were added concentrated HCl (2.0 mL) and Pd/C (10% wt, 850 mg). An H2 balloon was attached, and after evacuating and filling with H2 three times, the reaction was stirred at room temperature for 24 h. The black solution was then filtered through Celite and evaporated to give tert-butyl 4-[1-(aminomethyl)-2-methoxy-2-oxoethyl]benzoate hydrochloride as an off-white powder that was carried on without further purification. MS (ESI) calcd [M+H]+ 280.1, found 280.1.

Workup

  1. customafter evacuating
  2. filtrationThe black solution was then filtered through Celite
  3. customevaporated

Sources & evidence

ORD record
ord-1b0a9ca9e6f3435d88ce821ef1ccfc74
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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