Benzylamine → (3R,4S,5R)-5-benzylamino-3-(1-ethyl-propoxy)-4-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:7][C@H:8]2[C@@H:10]([C@H:11]([O:13][CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH:12]=1)[O:9]2)=[O:5])[CH3:2].O1CCCC1.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:1]([O:3][C:4]([C:6]1[CH2:7][C@@H:8]([NH:31][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:10]([OH:9])[C@H:11]([O:13][CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH:12]=1)=[O:5])[CH3:2]Participants
Procedure
To a solution of 5.08 g (20 mmol) (1S,5R,6S)-5-(1-ethyl-propoxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester in 20 ml tetrahydrofuran 1.03 g (4 mmol) magnesium bromide diethyl etherate was added at room temperature. The resulting suspension was treated with 4.40 ml (40 mmol) of benzylamine and heated to reflux under argon with stirring for 12 hours. The reaction mixture was evaporated in a rotary evaporator, the residue treated with 20 ml of ethyl acetate and extracted 6 times with 20 ml of 5N aqueous ammonium chloride solution. The organic phase was dried over 5 g of sodium sulfate, filtered and evaporated to yield 6.88 g of (3R,4S,5R)-5-benzylamino-3-(1-ethyl-propoxy)-4-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester as a brown oil.
Workup
- temperatureheated
- temperatureto reflux under argon
- customThe reaction mixture was evaporated in a rotary evaporator
- additionthe residue treated with 20 ml of ethyl acetate
- extractionextracted 6 times with 20 ml of 5N aqueous ammonium chloride solution
- dry with materialThe organic phase was dried over 5 g of sodium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-f4b786c5fd814cad83d5213f21b905f3
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06437171B1
Reaction notes
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