HCID 10599295, compound → HCID 10619631, compound

HRID 1603947Notes

Reaction equation

HRID 1603947 reaction equation
C(OC([NH:8][CH:9]([CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:12]=1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[CH3:31][CH:30]([CH3:32])[CH2:29][CH2:28][CH:9]([NH2:8])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:12]=1

Participants

4

Reactant 1

HCID 10599295HCID 10599295, compound

Product 1

HCID 10619631HCID 10619631, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of N-t-butoxycarbonyl-1-(3-methylbutyl)-2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine (89.69 g) in 156 ml of dichloromethane, 156 ml of trifluoroacetic acid was added and stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in dichloromethane and washed with a saturated aqueous solution of sodium hydrogencarbonate. The dichloromethane solution was dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified by silica gel column chromatography (chloroform/methanol =30:1-20:1), to thereby obtain 59.65 g of 1-(3-methylbutyl)-2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materialThe dichloromethane solution was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by silica gel column chromatography (chloroform/methanol =30:1-20:1)

Sources & evidence

ORD record
ord-12bfdb435cc84c459ef3e7d2db91487c
Source dataset
uspto-grants-1999_11
Patent number
US05990151

Reaction notes

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