Technology Process of 3-[Cyclopropyl-(3,5-diamino-phenyl)-methyl]-4-hydroxy-5,6,7,8,9,10-hexahydro-cycloocta[b]pyran-2-one
There total 6 articles about 3-[Cyclopropyl-(3,5-diamino-phenyl)-methyl]-4-hydroxy-5,6,7,8,9,10-hexahydro-cycloocta[b]pyran-2-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 43 percent / (dimethylamino)pyridine, pyridine / 0 - 20 °C
2: 65 percent / BH3*THF / tetrahydrofuran / 5.5 h / -10 °C
3: 1.) DMSO, oxalyl chloride, 2.) diisopropylethylamine / 1.) CH2Cl2, -30 deg C, 1 h, 2.) CH2Cl2, from -25 deg C to RT, 1 h
4: 1.) t-BuLi / 1.) THF, -78 deg C, 15 min, 2.) THF, from -78 deg C to RT, 1.5 h
5: 76 percent / p-toluenesulfonic acid, molecular sieves / CH2Cl2 / a) RT, 1.5 h, b) reflux, 1.5 h
6: 63 percent / H2 / 10percent Pd/C / ethanol / 1.25 h / 2068.6 Torr
With
pyridine; dmap; molecular sieve; borane-THF; oxalyl dichloride; hydrogen; tert.-butyl lithium; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/jm960441m
- Guidance literature:
-
Multi-step reaction with 3 steps
1: 1.) t-BuLi / 1.) THF, -78 deg C, 15 min, 2.) THF, from -78 deg C to RT, 1.5 h
2: 76 percent / p-toluenesulfonic acid, molecular sieves / CH2Cl2 / a) RT, 1.5 h, b) reflux, 1.5 h
3: 63 percent / H2 / 10percent Pd/C / ethanol / 1.25 h / 2068.6 Torr
With
molecular sieve; hydrogen; tert.-butyl lithium; toluene-4-sulfonic acid;
palladium on activated charcoal;
In
ethanol; dichloromethane;
DOI:10.1021/jm960441m
- Guidance literature:
-
Multi-step reaction with 4 steps
1: 1.) DMSO, oxalyl chloride, 2.) diisopropylethylamine / 1.) CH2Cl2, -30 deg C, 1 h, 2.) CH2Cl2, from -25 deg C to RT, 1 h
2: 1.) t-BuLi / 1.) THF, -78 deg C, 15 min, 2.) THF, from -78 deg C to RT, 1.5 h
3: 76 percent / p-toluenesulfonic acid, molecular sieves / CH2Cl2 / a) RT, 1.5 h, b) reflux, 1.5 h
4: 63 percent / H2 / 10percent Pd/C / ethanol / 1.25 h / 2068.6 Torr
With
molecular sieve; oxalyl dichloride; hydrogen; tert.-butyl lithium; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine;
palladium on activated charcoal;
In
ethanol; dichloromethane;
DOI:10.1021/jm960441m