Multi-step reaction with 11 steps
1.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C
2.1: sodium hydride / tetrahydrofuran
3.1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 0 °C
4.1: dichloromethane / 0 - 20 °C
5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride
5.2: 0 - 20 °C
6.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 0 - 20 °C
7.1: 1-hydroxy-7-aza-benzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate
7.2: 0 - 20 °C
8.1: tetrahydrofuran; dichloromethane / 0 - 20 °C
9.1: 1-hydroxy-7-aza-benzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate
9.2: 0 - 20 °C
10.1: water; lithium hydroxide / tetrahydrofuran / 0 - 20 °C
11.1: pyridine
With
pyridine; 1-hydroxy-7-aza-benzotriazole; lithium hydroxide monohydrate; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; dimethylsulfide borane complex; water; sodium hydride; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hydroxide; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole;
In
tetrahydrofuran; dichloromethane;
1.1: Dess-Martin oxidation;
DOI:10.1055/s-0030-1260806