Benzyl chloroformate → Benzyl (2,2-dimethoxyethyl)carbamate

HRID 338080Notes

Reaction equation

HRID 338080 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].[OH-].[Na+].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>C1(C)C=CC=CC=1>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH:5][C:11](=[O:12])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 10800009Benzyl (2,2-dimethoxyethyl)carbamateYield 98.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of aminoacetaldehyde dimethyl acetal (25 mL, 229 mmol) in toluene (120 mL) is treated at 0° C. with a 4.85 M sodium hydroxide solution (70.8 mL, 343.5 mmol). The mixture is stirred at 0° C. for 10 minutes and benzyl chloroformate (33.8 mL, 229 mmol) is added keeping the internal temperature below 20° C. during the addition. The mixture is warmed to room temperature over 4 hours. The organic layer is separated, washed with brine, dried over sodium sulfate, and concentrated to dryness to give the title compound (54 g, 98%). ES/MS (m/e): 240 (M+H).

Workup

  1. customthe internal temperature below 20° C.
  2. additionduring the addition
  3. temperatureThe mixture is warmed to room temperature over 4 hours
  4. customThe organic layer is separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-082b93a044f74468ae243a0a5afffadb
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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