tert-Butanol → tert-butyl N-(5-methyl-3-pyridyl)carbamate
Reaction equation
C[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=O.C([N:14]([CH2:18]C)C(C)C)(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])C=CC=CC=1.[C:37]([OH:41])([CH3:40])([CH3:39])[CH3:38]>>[C:37]([O:41][C:18](=[O:27])[NH:14][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH3:7])[CH:10]=1)([CH3:40])([CH3:39])[CH3:38]Participants
Conditions
- Temperature
- 80 °C
Procedure
5-Methyl-nicotinic acid (2 g, 14.6 mmol) was dissolved into t-Butanol (59 mL). To this was added N,N-Diisopropylethylamine (7.6 mL, 43.8 mmol) and diphenylphosphoryl azide (3.8 mL, 17.5 mmol). The reaction was heated to 80° C. overnight in a flask fitted with septa and argon gas line. The solvents were evaporated in vacuo and the resulting residue was dissolved into EtOAc, washed with saturated NaHCO3 and water. The combined organic layers were dried (MgSO4) and the solvents were removed in vacuo. The residue was purified by flash column chromatography (SiO2) (50% EtOAc in hexanes) that yielded the title compound as a white solid (2.03 g, 67%). 1H-NMR (CDCl3): δ 8.22 (m, 1H), 8.14 (m, 1H), 7.88 (br s, 1H), 6.58 (br s, 1H), 2.34 (s, 3H), 1.55 (s, 9H).
Workup
- customfitted with septa and argon gas line
- customThe solvents were evaporated in vacuo
- dissolutionthe resulting residue was dissolved into EtOAc
- washwashed with saturated NaHCO3 and water
- dry with materialThe combined organic layers were dried (MgSO4)
- customthe solvents were removed in vacuo
- customThe residue was purified by flash column chromatography (SiO2) (50% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-10dfe55a2c06487698cefe8bfa787be8
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109354B2
Reaction notes
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