Triethanolamine → (R)-1-(3-tert-butoxyphenyl)ethylamine

HRID 2425849Notes

Reaction equation

HRID 2425849 reaction equation
[C:1]([O:5][C:6]1[CH:7]=[C:8]([C@H:12]([NH:14]C(=O)COC)[CH3:13])[CH:9]=[CH:10][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].N(CCO)(CCO)CCO.[OH-].[Na+]>O>[C:1]([O:5][C:6]1[CH:7]=[C:8]([C@H:12]([NH2:14])[CH3:13])[CH:9]=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7618TriethanolamineHCID 14798Sodium HydroxideHCID 67255125N-[(1R)-1-(3-tert-Butoxyphenyl)ethyl]-2-methoxyacetamide

Product 1

HCID 55264960(R)-1-(3-tert-butoxyphenyl)ethylamineYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(R)—N-1-(3-tert-Butoxyphenyl)ethylmethoxyacetamide from example 2.3 (63.5 g with a purity of 93%; corresponds to 0.22 mol of pure substance) was mixed with triethanolamine (6 ml) with stirring and then admixed with 50% NaOH (23.2 g, 0.29 mol). The mixture was then stirred at a bath temperature of 140° C. for another 16 hours, after which all of the amide had reacted according to GC analysis. The mixture was diluted with water (100 ml), cooled and extracted with tert-butyl methyl ether (3×100 ml). The combined extracts were washed with saturated sodium chloride solution (50 ml) and dried over Na2SO4. After the solvent had been removed on a rotary evaporator, 41 g (92%) of (R)-1-(3-tert-butoxyphenyl)ethylamine were obtained in the form of a colorless oil. The chemical purity was 99.4%, the optical purity 98.9% ee.

Workup

  1. stirringThe mixture was then stirred at a bath temperature of 140° C. for another 16 hours
  2. temperaturecooled
  3. extractionextracted with tert-butyl methyl ether (3×100 ml)
  4. washThe combined extracts were washed with saturated sodium chloride solution (50 ml)
  5. dry with materialdried over Na2SO4
  6. customAfter the solvent had been removed on a rotary evaporator

Sources & evidence

ORD record
ord-0a0f4cce07de418fbcb44e933f76153c
Source dataset
uspto-grants-2011_06
Patent number
US07968328B2

Reaction notes

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