Ammonia → benzyl N-(2-cyanopropan-2-yl)carbamate
Reaction equation
[CH3:1][C:2]([CH3:6])(O)[C:3]#[N:4].[NH3:7].[C:8]([O-:11])([O-])=[O:9].[Na+].[Na+].ClC(OO[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O>CO.C(OCC)(=O)C>[C:3]([C:2]([NH:7][C:8](=[O:9])[O:11][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:6])[CH3:1])#[N:4]Participants
7
Conditions
- Temperature
- 10 °C
Procedure
Acetone cyanohydrin (17 grams, 200 mmol) was added to 400 mL of a 2M solution of NH3 in methanol and the resulting mixture stirred under N2 for 4 days. The solvent was removed in vacuo and the remaining residue dissolved in 250 mL of H2O. After cooling to 10° C., the solution was treated with Na2CO3 (21 grams, 200 mmol) and 95% benzyloxy chloroformate (33 mL, 230 mmol) and stirring continued overnight. Ethyl acetate was added and the mixture transferred to a seperatory funnel. The aqueous layer was removed and the ethyl acetate solution washed with saturated NaHCO3. After drying over Na2SO4 the solvent was removed to yield a solid which was triturated with hexanes to provide the title compound.
Workup
- customThe solvent was removed in vacuo
- dissolutionthe remaining residue dissolved in 250 mL of H2O
- stirringstirring continued overnight
- customthe mixture transferred to a seperatory funnel
- customThe aqueous layer was removed
- washthe ethyl acetate solution washed with saturated NaHCO3
- dry with materialAfter drying over Na2SO4 the solvent
- customwas removed
- customto yield a solid which
- customwas triturated with hexanes
Sources & evidence
- ORD record
- ord-fab6d0212a6e4ba18d0ec4281c48a046
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07192948B2
Reaction notes
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