Trifluoroacetic acid → (S)-3-(4-benzyloxy-phenyl)-N1,N1-diethyl-propane-1,2-diamine

HRID 278889Notes

Reaction equation

HRID 278889 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:24][N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[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:12]=[CH:11][C:10]([CH2:9][C@H:8]([NH2:7])[CH2:24][N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[CH:15][CH:14]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18711795[2-(4-Benzyloxy-phenyl)-1-(diethylamino-methyl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 59973358(S)-3-(4-benzyloxy-phenyl)-N1,N1-diethyl-propane-1,2-diamineYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 171 mg (0.4 mmol) [2-(4-benzyloxy-phenyl)-1-(diethylamino-methyl)-ethyl]-carbamic acid tert-butyl ester in 2 mL dichloromethane was treated with 0.5 mL 2,2,2-triflouroacetic acid and the resulting solution stirred 3 hours at 25° C. The mixture was concentrated at reduced pressure to a viscous amber oil to which was added 30 mL saturated aqueous sodium bicarbonate solution and the resulting mixture extracted with three 20 mL portions of ethyl acetate. The combined extracts were washed with two 50 mL portions of brine, dried over anhydrous sodium sulfate, and concentrated at reduced pressure and the residue purified by column chromatography using ethyl acetate containing 1% methanol as eluent. There was obtained 112 mg (90%) of (S)-3-(4-benzyloxy-phenyl)-N1,N1-diethyl-propane-1,2-diamine as a clear, colorless oil.

Workup

  1. concentrationThe mixture was concentrated at reduced pressure to a viscous amber oil to which
  2. additionwas added 30 mL saturated aqueous sodium bicarbonate solution
  3. extractionthe resulting mixture extracted with three 20 mL portions of ethyl acetate
  4. washThe combined extracts were washed with two 50 mL portions of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated at reduced pressure
  7. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-74d4c9ba9b954a1082f57be9e3135433
Source dataset
uspto-grants-2002_03
Patent number
US06362174B1

Reaction notes

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