Trifluoroacetic acid → (S)-2-(4-benzyloxy-phenyl)-1-morpholin-4-ylmethyl-ethylamine

HRID 429130Notes

Reaction equation

HRID 429130 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:17]([O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][C@H:8]([NH2:7])[CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:11][CH:12]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18711796[2-(4-Benzyloxy-phenyl)-1-morpholin-4-ylmethyl-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 70090603(S)-2-(4-benzyloxy-phenyl)-1-morpholin-4-ylmethyl-ethylamineYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 1.41 g (3.3 mmol) [2-(4-benzyloxy-phenyl)-1-morpholin-4-ylmethyl-ethyl]-carbamic acid tert-butyl ester in 5 mL dichloromethane was treated with 1.5 mL 2,2,2-triflouroacetic acid and the resulting solution stirred 16 hours at 25° C. The mixture was concentrated at reduced pressure to a viscous amber oil to which was added 50 mL saturated aqueous sodium bicarbonate solution and the resulting mixture extracted with three 50 mL portions of ethyl acetate. The combined extracts were washed with 100 mL brine, dried over anhydrous sodium sulfate and concentrated at reduced pressure affording a soft solid, that was recrystallized from 2,2,4-trimethylpentane containing about 5% ethyl acetate to afford 804 mg (77%) of (S)-2-(4-benzyloxy-phenyl)-1-morpholin-4-ylmethyl-ethylamine as light tan crystals; mp 180-182° C.

Workup

  1. concentrationThe mixture was concentrated at reduced pressure to a viscous amber oil to which
  2. additionwas added 50 mL saturated aqueous sodium bicarbonate solution
  3. extractionthe resulting mixture extracted with three 50 mL portions of ethyl acetate
  4. washThe combined extracts were washed with 100 mL brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated at reduced pressure
  7. customaffording a soft solid, that
  8. customwas recrystallized from 2,2,4-trimethylpentane containing about 5% ethyl acetate

Sources & evidence

ORD record
ord-9b3319170445422bbcf08b54db657835
Source dataset
uspto-grants-2001_11
Patent number
US06316440B1

Reaction notes

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