(4R,9aR)-6-Formyl-4-methyl-3,4,9,9a-tetrahydro-1 H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester → (4R,9aR)-6-(1-(RS)-Hydroxy-ethyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH:22]=[O:23])=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][Mg]Br>O1CCCC1.CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH:22]([OH:23])[CH3:24])=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 10.00 g (4R,9aR)-6-Formyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 100 ml tetrahydrofuran was added drop wise at 0° C. 20 ml of a ca 3M solution of methyl magnesium bromide solution in ether. The mixture was stirred at 0° C. for 30 min. The reaction mixture was quenched with 10% aqueous ammonium chloride and extracted with ethyl acetate. The organic phase was washed with 105 aqueous citric acid, 10% aqueous sodium bicarbonate and brine, dried over sodium sulfate, evaporated and dried to constant weight under high vacuum to yield 10.0 g of the title compound as colorless oil (MS: 334.5 (M+H+)).
Workup
- customThe reaction mixture was quenched with 10% aqueous ammonium chloride
- extractionextracted with ethyl acetate
- washThe organic phase was washed with 105 aqueous citric acid, 10% aqueous sodium bicarbonate and brine
- dry with materialdried over sodium sulfate
- customevaporated
- customdried to constant weight under high vacuum
Sources & evidence
- ORD record
- ord-58909f9ce80748f995ee31be93d6cbcb
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07547699B2
Reaction notes
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