Multi-step reaction with 11 steps
1.1: potassium carbonate / methanol; tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
2.1: pyridine / tetrahydrofuran; toluene / 2 h / -78 - -40 °C / Inert atmosphere
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
3.2: 1.5 h / -78 °C / Inert atmosphere
4.1: toluene-4-sulfonic acid / methanol / 8 h / 20 °C / Inert atmosphere
5.1: pyridine; pyridine hydrochloride / 23 h / 100 °C / Inert atmosphere
6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
6.2: 2 h / 0 - 20 °C / Inert atmosphere
7.1: ammonia; sodium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere
8.1: tetrahydrofuran; water / 4.5 h / 0 - 20 °C / Inert atmosphere
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere
10.1: pyridine / 1 h / 0 - 20 °C / Inert atmosphere
11.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C / Inert atmosphere
11.2: 3 h / 90 °C / Inert atmosphere
With
pyridine; lithium aluminium tetrahydride; oxalyl dichloride; ammonia; pyridine hydrochloride; sodium; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; 9-bora-bicyclo[3.3.1]nonane;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
3.1: |Swern Oxidation / 3.2: |Swern Oxidation / 7.1: |Birch Reduction;
DOI:10.1021/acs.orglett.6b00661