Hydrochloric Acid → tert-butyl N-(2-hydroxy-2-phenylethyl)carbamate

HRID 1354394Notes

Reaction equation

HRID 1354394 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].[CH3:11][C:12]([O:15][C:16](=O)[O:17]C(C)(C)C)([CH3:14])[CH3:13].C(=O)([O-])[O-].[Na+].[Na+].Cl>CO>[OH:4][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][NH:1][C:16](=[O:17])[O:15][C:12]([CH3:14])([CH3:13])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1000PhenylethanolamineHCID 10340Sodium CarbonateHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 9816137tert-butyl N-(2-hydroxy-2-phenylethyl)carbamateYield 116.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Racemic α-(aminomethyl)benzenemethanol (13.7 g) and bis(1,1-dimethylethyl)carbonate (21.8 g) were dissolved in methanol (200 ml) and 10% aqueous sodium carbonate (200 ml) added. The mixture was stirred at room temperature for 24 h, poured into 2M hydrochloric acid and extracted with ethyl acetate. Evaporation of the extract and trituration with ethyl acetate/hexane gave the sub-title compound as a pale yellow solid (27.6 g).

Workup

  1. extractionextracted with ethyl acetate
  2. customEvaporation of the
  3. extractionextract

Sources & evidence

ORD record
ord-09ceacc461314eb59ea04a67de6860b5
Source dataset
uspto-grants-2007_05
Patent number
US07223794B2

Reaction notes

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