Iodine → tert-butyl 3-((5-tert-butyl-2-iminothiazol-3(2H)-yl)methyl)azetidine-1-carboxylate
Reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH:4]=O.[NH2:8][CH2:9][CH:10]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]1.[S-:21][C:22]#[N:23].[K+].II>C(#N)C>[C:2]([C:3]1[S:21][C:22](=[NH:23])[N:8]([CH2:9][CH:10]2[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]2)[CH:4]=1)([CH3:7])([CH3:6])[CH3:1]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
3,3-Dimethylbutanal (0.7 mL, 5.4 mmol), tert-butyl 3-(aminomethyl)azetidine-1-carboxylate (Astatech, 1.0 g, 5.4 mmol) were mixed with 2 g of 4 Å molecular sieves in 5 mL of dry acetonitrile at room temperature for 20 hours. The reaction was filtered through Celite, washed with 5 mL of acetonitrile and the filtrate used without further purification. Potassium thiocyanate (0.7 g, 7.1 mmol) was added and the mixture heated to 50° C. for 10 minutes. Iodine (1.4 g, 5.4 mmol) was added and the reaction mixture was continued to stir at 50° C. for 6 hours. The reaction mixture was cooled to room temperature, 10 mL of acetonitrile was added, followed by 10 mL of 20% Na2S2O5. The phases were separated and the organic phase was dried with Na2SO4, filtered, and the solvent removed to provide the title compound. LC/MS m/z 326.3 (M+H)+. The product was used without further purification.
Workup
- filtrationThe reaction was filtered through Celite
- washwashed with 5 mL of acetonitrile
- customthe filtrate used without further purification
- temperatureThe reaction mixture was cooled to room temperature
- customThe phases were separated
- dry with materialthe organic phase was dried with Na2SO4
- filtrationfiltered
- customthe solvent removed
Sources & evidence
- ORD record
- ord-9e147e6b443240b59e9d3fdaf24ef2e9
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338467B2
Reaction notes
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