(R)-tert-Butyl (oxiran-2-ylmethyl)carbamate → (3-Amino-2-hydroxy-propyl)-carbamic acid tert-butyl ester

HRID 1811738Notes

Reaction equation

HRID 1811738 reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][C@@H:9]1[CH2:11][O:10]1)([CH3:4])([CH3:3])[CH3:2].O.[NH3:14]>C(O)C>[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][C@@H:9]([OH:10])[CH2:11][NH2:14])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10464779(R)-tert-Butyl (oxiran-2-ylmethyl)carbamateHCID 12896473Azane;hydrate

Product 1

HCID 86639750(3-Amino-2-hydroxy-propyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-1-Oxiranylmethylcarbamic acid tert-butyl ester (2.26 g, 13.05 mmol) obtained in Step 2 above was dissolved in ethanol (15 ml), and then 28% ammonia water (6 ml) was added thereto at room temperature. After the solution was stirred at room temperature for 1.5 hour, the solvent was distilled off under reduced pressure. After the resulting residue was dissolved in methanol, the solvent was distilled off under reduced pressure to give a crude product of ((S)-3-amino-2-hydroxypropyl)carbamic acid tert-butyl ester (2.38 g) as a yellow oily material.

Workup

  1. customat room temperature
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionAfter the resulting residue was dissolved in methanol
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-57297dafbb8d47b2b63ad80ded3b37ee
Source dataset
uspto-grants-2013_01
Patent number
US08362236B2

Reaction notes

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