1.1
Reagents:
Selenium dioxide
;
rt → 160 °C; 20 h, 160 °C
2.1
Reagents:
Piperidine, 2,2,6,6-tetramethyl-, lithium salt (1:1)
Solvents:
Tetrahydrofuran
,
Hexane
;
25 min, -78 °C
2.2
Solvents:
Tetrahydrofuran
;
5 min, -78 °C; 2 h, -78 °C; 30 min, -78 °C → 0 °C
2.3
Reagents:
Citric acid
Solvents:
Water
3.1
Reagents:
Thionyl chloride
Solvents:
Chloroform
;
10 min, -4 °C; 4 h, -4 °C → rt
3.2
Reagents:
Potassium phthalimide
Solvents:
Dimethylformamide
;
rt → 60 °C; 16 h, 60 °C
3.3
Reagents:
Hydrazine
Solvents:
Ethanol
,
Dichloromethane
;
16 h, rt
4.1
Reagents:
1-Hydroxybenzotriazole
,
Diisopropylethylamine
,
1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride
Solvents:
Dichloromethane
;
16 h, rt
5.1
Reagents:
Phosphorus oxychloride
Solvents:
Acetonitrile
;
5 min, rt
5.2
Catalysts:
Dimethylformamide
;
rt; 2 h, 55 °C
5.3
Reagents:
Ammonia
Solvents:
Isopropanol
,
Dichloromethane
;
pH 9
6.1
Reagents:
N-methylmorpholine N-oxide
Catalysts:
Potassium osmate dihydrate
Solvents:
Tetrahydrofuran
,
Water
;
20 h, rt
6.2
Reagents:
Sodium sulfite
;
10 min, rt
6.3
Reagents:
Sodium periodate
Solvents:
Tetrahydrofuran
,
Water
;
0 °C; 4 h, 0 °C → rt