Hydrochloric Acid → (R)-2-Amino-2-(naphthalen-2-yl)ethanol hydrochloride

HRID 857026Notes

Reaction equation

HRID 857026 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)[CH2:9][OH:10])(C)(C)C.[ClH:22]>C(OCC)(=O)C>[ClH:22].[NH2:7][C@H:8]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)[CH2:9][OH:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57419701(R)-(2-Hydroxy-1-naphthalen-2-yl-ethyl)-carbamic acid tert-butyl ester

Product 1

HCID 57462036(R)-2-Amino-2-(naphthalen-2-yl)ethanol hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-(2-Hydroxy-1-naphthalen-2-yl-ethyl)-carbamic acid tert-butyl ester (2.5 g) and 9 mL of 4 N HCl in ethyl acetate at 50° C. was stirred for 2 h. After concentration, the residue was neutralized with 10 N NaOH and extracted with methylene chloride. The organic layer was washed with brine, dried over Na2SO4, and concentrated to give the title compound (1.2 g) as a solid which was used in the next step without further purification.

Workup

  1. concentrationAfter concentration
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f388d190d9db4f81adbcdec40d8a0a90
Source dataset
uspto-grants-2006_12
Patent number
US07144881B2

Reaction notes

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