Multi-step reaction with 11 steps
1: 1) NaH / 1) THF, 0 to 20 deg C, 2) THF, -78 to -15 deg C, 3 h
2: 74 percent / K2CO3 / methanol / 0.5 h / Ambient temperature
3: DIBAH / toluene / 0.17 h / -80 °C
4: CSA / 0.25 h / Ambient temperature
5: hydrogen / Raney Ni (W-2) / ethanol / 2 h / Ambient temperature
6: hydrogen / 5percent Rh-Al2O3 / diethyl ether / 3.5 h
7: 1) DMSO, (COCl)2, 2) Et3N / 1) CH2Cl2, -70 deg C, 2) CH2Cl2, -70 to 0 deg C
8: diethyl ether / -50 - 0 °C
9: 1) NaH / 1) DMF, RT, 2) DMF, 50 deg C, 18 h
10: 80 percent / 0.4N HCl / tetrahydrofuran / 16 h / 55 °C
11: 94 percent / pyridinium chlorochromate, mol. sieves 3A / CH2Cl2 / 2 h / Ambient temperature
With
hydrogenchloride; oxalyl dichloride; 3 A molecular sieve; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate;
rhodium on alumina; Raney Ni (W-2);
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene;
DOI:10.1248/cpb.37.1698