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

HRID 429132Notes

Reaction equation

HRID 429132 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-8aee0b5c5fdd4bf2873b509d1e7cc23f
Source dataset
uspto-grants-2001_11
Patent number
US06316440B1

Reaction notes

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