Formamide → 4-hydroxy-N-methylproline
Reaction equation
[CH2:1]1[C@@H:5]([C:6]([OH:8])=[O:7])[NH:4][CH2:3][C@@H:2]1[OH:9].[CH:10](N)=O.[H][H]>[Pd].O.C(O)C>[OH:9][C@H:2]1[CH2:3][N:4]([CH3:10])[C@H:5]([C:6]([OH:8])=[O:7])[CH2:1]1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
A suspension of (2S,4R)-trans-4-hydroxyproline (5 g), 37% aqueous formamide solution (4.6 g) and 7.5% palladium on charcoal (53% water content, 3.2 g) in water (15 mL) was stirred at room temperature in an atmosphere of high-pressure hydrogen for 10 hours. After removing the palladium on charcoal by filtration, the water of the filtrate was removed by distillation under reduced pressure. The solid residue thus obtained was suspended and stirred in ethanol (25 mL). The crystals which precipitated were collected by filtration to give the title compound (5.1 g, yield 92%).
Workup
- customAfter removing the palladium on charcoal
- filtrationby filtration
- customthe water of the filtrate was removed by distillation under reduced pressure
- customThe solid residue thus obtained
- customThe crystals which precipitated
- filtrationwere collected by filtration
Sources & evidence
- ORD record
- ord-9c8bc77dc55d4a88890aa30b737c9dda
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091363B2
Reaction notes
Loading…
