Hydrochloric Acid → 5-(3-Amino-propyl)-thiophene-2-carboxylic acid tert-butyl ester hydrochloride

HRID 2298210Notes

Reaction equation

HRID 2298210 reaction equation
[C:1]([O:5][C:6]([C:8]1[S:9][C:10]([C:13]#[C:14][CH2:15][NH:16]C(OCC2C=CC=CC=2)=O)=[CH:11][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[ClH:27]>CO.[OH-].[OH-].[Pd+2]>[ClH:27].[C:1]([O:5][C:6]([C:8]1[S:9][C:10]([CH2:13][CH2:14][CH2:15][NH2:16])=[CH:11][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 545289645-(3-Benzyloxycarbonylamino-prop-1-ynyl)-thiophene-2-carboxylic acid tert-butyl ester

Product 1

HCID 695442585-(3-Amino-propyl)-thiophene-2-carboxylic acid tert-butyl ester hydrochloride

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-(3-benzyloxycarbonylamino-prop-1-ynyl)-thiophene-2-carboxylic acid tert-butyl ester (1.0 g, 2.69 mmol) in 15 mL MeOH and 2.69 mL 1N HCl (aq) was added Pd(OH)2 (1 g). The mixture was shaken in a Parr shaker under 45 psi H2 for 16 h. The catalyst was removed by filtration through Celite and additional Pd(OH)2 (1 g) was added. The reaction was shaken at 45 psi H2 for 6 h and the catalyst was removed by filtration through Celite. The solution was concentrated in vacuo. The residue was azeotroped with CCl4 and was triturated with Et2O to provide the title amine (360 mg).

Workup

  1. customThe catalyst was removed by filtration through Celite and additional Pd(OH)2 (1 g)
  2. additionwas added
  3. stirringThe reaction was shaken at 45 psi H2 for 6 h
  4. customthe catalyst was removed by filtration through Celite
  5. concentrationThe solution was concentrated in vacuo
  6. customThe residue was azeotroped with CCl4
  7. customwas triturated with Et2O

Sources & evidence

ORD record
ord-6f97ee0edad84a1f82a15cdf3883c1ea
Source dataset
uspto-grants-2002_12
Patent number
US06492412B2

Reaction notes

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