Trifluoroacetic acid → (R)-2-Amino-2-(7-methoxy-naphthalen-2-yl)-ethanol

HRID 1825046Notes

Reaction equation

HRID 1825046 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C@H:15]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][C:22]([O:28][CH3:29])=[CH:23][CH:24]=2)[CH:19]=1)[CH2:16][OH:17])(C)(C)C>C(Cl)Cl>[NH2:14][C@H:15]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][C:22]([O:28][CH3:29])=[CH:23][CH:24]=2)[CH:19]=1)[CH2:16][OH:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58633313(R)-[2-hydroxy-1-(7-methoxy-naphthalen-2-yl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 58633291(R)-2-Amino-2-(7-methoxy-naphthalen-2-yl)-ethanolYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of TFA (8 mL) and (R)-[2-hydroxy-1-(7-methoxy-naphthalen-2-yl)-ethyl]-carbamic acid tert-butyl ester (1.268 g) in methylene chloride (24 mL) 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 as a solid (860 mg).

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-20d027a6be6a4eb98686000c21426b9f
Source dataset
uspto-grants-2006_05
Patent number
US07045551B2

Reaction notes

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