Hydrochloric Acid → (3R)-3-[5-{2-[3-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine

HRID 1433272Notes

Reaction equation

HRID 1433272 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:21]([C@@H:33]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:34][CH2:35][N:36]([CH:40]([CH3:42])[CH3:41])[CH:37]([CH3:39])[CH3:38])[CH:20]=2)[CH:11]=1)(C)(C)C.Cl>ClCCl>[NH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=1)[O:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:21]([C@@H:33]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH2:34][CH2:35][N:36]([CH:37]([CH3:39])[CH3:38])[CH:40]([CH3:42])[CH3:41])[CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57933226tert-butyl {2-[3-(2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethoxy)phenyl]ethyl}carbamate

Product 1

HCID 57933181(3R)-3-[5-{2-[3-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl{2-[3-(2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethoxy)phenyl]ethyl}carbamate (Preparation 37, 1.3 g, 2.0 mmol) dissolved in dichloromethane (5 ml) and hydrochloric acid (4M in dioxin) added. Mixture stirred at room temperature for 3 hours under nitrogen. Solvent was removed in vacuo, and residue dissolved in dichloromethane (100 ml) and aqueous sodium hydroxide (1M, 100 ml), aqueous separated and extracted with dichloromethane (100 ml). Combined organics were dried (magnesium sulphate) and the solvent was removed in vacuo to furnish the title compound as an oil, 880 mg.

Workup

  1. customSolvent was removed in vacuo, and residue
  2. dissolutiondissolved in dichloromethane (100 ml)
  3. customaqueous sodium hydroxide (1M, 100 ml), aqueous separated
  4. extractionextracted with dichloromethane (100 ml)
  5. dry with materialCombined organics were dried (magnesium sulphate)
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4780fee0199d45cd87e67b8c87fbf339
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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