Tetrahydrofuran → (1RS,2SR,6RS)-2-Hydroxymethyl-8-azabicyclo[4.3.0]non-4-ene
Reaction equation
[NH2:1][CH2:2]/[CH:3]=[CH:4]/[CH:5]=[CH2:6].[CH2:7]1[CH2:11][O:10][CH2:9][CH2:8]1>>[OH:10][CH2:11][CH:7]1[CH2:6][CH:5]=[CH:4][CH:3]2[CH:8]1[CH2:9][NH:1][CH2:2]2Participants
Procedure
Initially introduce 83.2 g (1.0 mol) of (E)-1-amino-2,4-pentadiene (title compound from Example B.2.) in 250 ml of THF, and add 0.1 g of 4-hydroxyanisole. Subsequently, at an internal temperature of 20°-30° C., add 229.2 g (1.05 mol) of di-tert-butyl dicarbonate dissolved in 250 ml of THF dropwise. After addition is complete, stir at room temperature for 20 h. Add 103.0 g (1.05 mol) of maleic anhydride, and heat to reflux for 5 h. Concentrate and take up the residue in 500 ml of methanol, add 30 ml of p-toluenesulphonic acid, and then heat once again to reflux for 5 h. After cooling with ice, and stirring, rapidly add a solution of 20 g of sodium carbonate dissolved in 500 ml of water dropwise, allow the mixture to stand for a further 30 min in an ice bath, and filter off the precipitate with suction, wash it with a little water, and dry it at 50° C. to constant weight.
Sources & evidence
- ORD record
- ord-c53495a50d304fe180ffcba6e01c83d4
- Source dataset
- uspto-grants-1998_04
- Patent number
- US05739339
Reaction notes
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