Benzyl chloroformate → (1-Methoxymethyl-propyl)-carbamic acid benzyl ester
Reaction equation
[CH3:1][O:2][CH2:3][CH:4]([NH2:7])[CH2:5][CH3:6].C([O-])([O-])=O.[K+].[K+].[C:14](Cl)([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>O1CCOCC1>[CH2:17]([O:16][C:14](=[O:15])[NH:7][CH:4]([CH2:3][O:2][CH3:1])[CH2:5][CH3:6])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1-methoxymethyl-propylamine (2.50 g, 24.3 mmol, 1.0 eq.) in dioxane (15 mL) was added an aqueous solution of K2CO3 (15 g in 15 mL of H2O) and the mixture was cooled to 0° C. CBZ—Cl (4.16 mL, 1.2 eq.) was then introduced and the resulting mixture was warmed to room temperature and stirred for 3 h, extracted with EtOAc. The combined organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography (hexanes to 40% EtOAc/hexanes) to give (1-methoxymethyl-propyl)-carbamic acid benzyl ester (4.4 g, 76%) as a white solid.
Workup
- temperaturethe resulting mixture was warmed to room temperature
- extractionextracted with EtOAc
- dry with materialThe combined organic phase was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by chromatography (hexanes to 40% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-0c5783345d2b4f06ba9a8d68b84ffb29
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691814B2
Reaction notes
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