2-Methyltetrahydrofuran → benzyl (2,2-dimethoxyethyl)carbamate

HRID 575859Notes

Reaction equation

HRID 575859 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][O:8][CH:9]([O:13][CH3:14])[CH2:10][NH:11][CH3:12].CC1OCCC1.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>O>[CH2:25]([O:24][C:22](=[O:23])[N:11]([CH2:10][CH:9]([O:13][CH3:14])[O:8][CH3:7])[CH3:12])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 73012-MethyltetrahydrofuranHCID 85032,2-DimethoxyethylmethylamineHCID 10387Benzyl chloroformateHCID 11430Potassium Carbonate

Product 1

HCID 58058121benzyl (2,2-dimethoxyethyl)carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

K2CO3 (13.8 g, 100 mmol, 1.76 eq.) and H2O (46 mL) were mixed to form a homogeneous solution. The solution was cooled to 20° C. N-methylaminoacetaldehyde dimethylacetal (12.8 mL, 100 mmol, 1.8 eq) and MeTHF (50 mL) were added. The resulting mixture was cooled to 2° C. Benzyl chloroformate (8.1 mL, 56.7 mmol, 1.0 eq.) was added by syringe over 10 minutes (addition was exothermic). The mixture was maintained at room temperature until completion of the reaction. The layers were separated and the organic layer was washed with 1N HCl (50 mL) and used directly in the next step.

Workup

  1. customto form a homogeneous solution
  2. temperatureThe resulting mixture was cooled to 2° C
  3. addition(addition was exothermic)
  4. temperatureThe mixture was maintained at room temperature until completion of the reaction
  5. customThe layers were separated
  6. washthe organic layer was washed with 1N HCl (50 mL)

Sources & evidence

ORD record
ord-d5ae06f0f680429a95e865175cbd06e8
Source dataset
uspto-grants-2015_05
Patent number
US09035061B2

Reaction notes

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