Riboflavin → 2-(Trifluoromethyl)-1,2,3-propanetriol
Reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]([CH2:14][O:15]CC1C=CC=CC=1)([OH:13])[CH2:4][O:5]CC1C=CC=CC=1.CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C.[H][H]>C(O)C.[Pd]>[F:1][C:2]([F:24])([F:23])[C:3]([OH:13])([CH2:14][OH:15])[CH2:4][OH:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 1,1,1-trifluoro-3-[(benzyl)oxy]-2-{[(benzyl)oxy]methyl}-2-propanol (98.9 g, 290.9 mmol) in ethanol (1750 ml) was added to 5% palladium on carbon (9.73 g, wet, Degussa, E101 No/W) under nitrogen. The mixture was then stirred under an atmosphere of hydrogen using a Wright valve in a 5 liter hydrogenation vessel. After approximately 3 hours most of the theoretical volume of hydrogen had been taken up. After stirring under hydrogen overnight (approximately a further 1 liter of hydrogen had been taken up overnight), the catalyst was filtered off through a pad of celite and the pad washed with ethanol. The filtrate and washings were then concentrated under reduced pressure and the residue azeotroped (×2) with dichloromethane whereupon the residue became solid. This material was left on the vacuum pump to give the title compound (48.56 g) as an off white solid.
Workup
- filtration), the catalyst was filtered off through a pad of celite
- washthe pad washed with ethanol
- concentrationThe filtrate and washings were then concentrated under reduced pressure
- customthe residue azeotroped (×2) with dichloromethane whereupon the residue
- waitThis material was left on the vacuum pump
Sources & evidence
- ORD record
- ord-8440ce1aa5f94802a80e5d499ec5c8e2
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247377B2
Reaction notes
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