1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86624407, compound
Reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([C:12]1[CH:13]=[N:14][C:15]([O:18][CH3:19])=[N:16][CH:17]=1)O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C=CC(OP(OC2C=CC=CC=2)([N:29]=[N+:30]=[N-:31])=O)=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[N:29]([C@@H:10]([C:12]1[CH:13]=[N:14][C:15]([O:18][CH3:19])=[N:16][CH:17]=1)[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[N+:30]=[N-:31]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of (R)-2-(tert-butyldimethylsilyloxy)-1-(2-methoxypyrimidin-5-yl)ethanol (4.4 g, 15 mmol) and diphenylphosphonic azide (16.7 mL, 77.3 mmol) was dissolved in toluene (53 mL). The mixture was cooled to 0° C. and neat 1,8-diazabicyclo[5.4.0]undec-7-ene (11.8 mL, 77.3 mmol) was added. The reaction was stirred for 30 minutes at 0° C. and then reacted at 60° C. overnight. The mixture was washed with water (50 mL) and 5% HCl (50 mL). The organic layer was concentrated in vacuo and purified by silica gel chromatography (0-25% EtOAc/hexane) to afford a colorless oil.
Workup
- customreacted at 60° C. overnight
- washThe mixture was washed with water (50 mL) and 5% HCl (50 mL)
- concentrationThe organic layer was concentrated in vacuo
- custompurified by silica gel chromatography (0-25% EtOAc/hexane)
- customto afford a colorless oil
Sources & evidence
- ORD record
- ord-985a0c76e4a140a9b5dc505b46d5104b
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08076345B2
Reaction notes
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