5-(3-Benzyloxycarbonylamino-prop-1-ynyl)-thiophene-2-carboxylic acid tert-butyl ester → 5-(3-Amino-propyl)-thiophene-2-carboxylic acid tert-butyl ester

HRID 842739Notes

Reaction equation

HRID 842739 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]>CO.Cl.[OH-].[OH-].[Pd+2]>[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 1

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

Product 1

HCID 541907515-(3-Amino-propyl)-thiophene-2-carboxylic acid tert-butyl esterYield 55.5%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 313Hydrochloric AcidSolventHCID 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. The mixture was placed on a Parr shaker and was hydrogenated under 45 psi H2 for 16 h. The mixture was filtered through Celite®, the catalyst was replaced, and the reaction was shaken for another 6 h. The mixture was filtered through Celite® and concentrated in vacuo. The residue was chased with CCl4 and was triturated with Et2O. The product was isolated as a solid (360 mg).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. filtrationThe mixture was filtered through Celite®
  3. concentrationconcentrated in vacuo
  4. customwas triturated with Et2O

Sources & evidence

ORD record
ord-ed8eec6503044825b6d75987f6eb094b
Source dataset
uspto-grants-2002_04
Patent number
US06376502B1

Reaction notes

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