反应详情

1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-L-prolinamide (24 g, 0.060 mol) was dissolved in MeOH (500 mL) and degassed. Catalyst (10% Pd/C, Degussa type, wet, 2.4 g) was added and the mixture was stirred under a hydrogen balloon for 3 hours. After degassing, the suspension was filtered through Celite, washing with methanol, and the filtrate was concentrated. The resulting foam was dissolved in ethyl acetate (50 mL) and diluted with toluene (˜500 mL.) This solution was then concentrated to a slurry (˜100 mL) and diluted with hexanes (200 mL.) Filtration, washing with hexanes and drying afforded the product 1-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-L-prolinamide (21 g, 113% yield). The excess yield is due to residual toluene. LC/MS m/z 312 (MH+)

1. customdegassed
2. additionCatalyst (10% Pd/C, Degussa type, wet, 2.4 g) was added
3. customAfter degassing
4. filtrationthe suspension was filtered through Celite
5. washwashing with methanol
6. concentrationthe filtrate was concentrated
7. dissolutionThe resulting foam was dissolved in ethyl acetate (50 mL)
8. additiondiluted with toluene (˜500 mL.) This solution
9. concentrationwas then concentrated to a slurry (˜100 mL)
10. additiondiluted with hexanes (200 mL.) Filtration
11. washwashing with hexanes
12. customdrying