3,4-dihydro-2H-pyran → Cyclohexylisopropylamine
Reaction equation
O1C=C[CH2:4][CH2:3][CH2:2]1.Cl.[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:14]([Li])CCC>C(Cl)Cl.O1CCCC1>[CH:3]([NH:8][CH:13]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:14]1)([CH3:4])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Refer to Chart 0. The formula-CXIX 2-phenyl selenidyl compound is first prepared. The starting material is the methyl ester of (5E)-6a-carba-PGI2 (Example 23, 0.4 g.) which is converted to the formula-CXVIII bis(tetrahydropyran-2-yl ether) by reaction with dihydropyran in methylene chloride in the presence of pyridine hydrochloride following the procedure of Example 39-II. A solution of that bis(THP) methyl ester in 5 ml. of tetrahydrofuran is added dropwise to the amide formed from N-isopropylcyclohexylamine (0.3 g.) and n-butyllithium (equivalent 1.6 M hexane solution) in tetrahydrofuran (7 ml.) cooled to -78° C. The mixture is stirred at -78° C. for 45 min. and then phenylselenyl chloride is added in tetrahydrofuran solution over a 7 minute period. The mixture is stirred at -78° C. for an additional hour, then poured into 30 ml. of saturated ammonium chloride-ice-water mixture and extracted with diethyl ether. The organic phase is dried and concentrated. The residue is chromatographed on silica gel, eluting with ethyl acetate-toluene (1:8) to give the formula-CXIX compound.
Sources & evidence
- ORD record
- ord-ee1dba3692484737b72e56d54ed81797
- Source dataset
- uspto-grants-1980_12
- Patent number
- US04238414
Reaction notes
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