(1R,2S)-1-azido-1-[3,5-bis(trifluoromethyl)phenyl]-N-{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)bi phenyl-2-yl]methyl}propan-2-amine → (1R,2S)-1-[3,5-bis(trifluoromethyl)phenyl]-N2-{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}propane-1,2-diamine

HRID 1028541Notes

Reaction equation

HRID 1028541 reaction equation
[N:1]([C@H:4]([C:30]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[C:32]([C:40]([F:43])([F:42])[F:41])[CH:31]=1)[C@@H:5]([NH:7][CH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1[C:19]1[CH:24]=[C:23]([CH:25]([CH3:27])[CH3:26])[CH:22]=[CH:21][C:20]=1[O:28][CH3:29])[CH3:6])=[N+]=[N-]>C1COCC1.O=[Pt]=O>[F:37][C:36]([F:38])([F:39])[C:34]1[CH:35]=[C:30]([C@@H:4]([NH2:1])[C@@H:5]([NH:7][CH2:8][C:9]2[CH:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:12]=[CH:11][C:10]=2[C:19]2[CH:24]=[C:23]([CH:25]([CH3:26])[CH3:27])[CH:22]=[CH:21][C:20]=2[O:28][CH3:29])[CH3:6])[CH:31]=[C:32]([C:40]([F:41])([F:43])[F:42])[CH:33]=1

Participants

4

Reactant 1

HCID 86603414(1R,2S)-1-azido-1-[3,5-bis(trifluoromethyl)phenyl]-N-{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)bi phenyl-2-yl]methyl}propan-2-amine

Product 1

HCID 59135060(1R,2S)-1-[3,5-bis(trifluoromethyl)phenyl]-N2-{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}propane-1,2-diamine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R,2S)-1-azido-1-[3,5-bis(trifluoromethyl)phenyl]-N-{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}propan-2-amine (17.8 mg, 0.0288 mmol) in THF (3 mL) was added PtO2 (12 mg, 0.053 mmol). The reaction was placed under hydrogen balloon atmosphere and stirred at room temperature for 3 h. The catalyst was removed by filtration and the filtrate was concentrated. The residue was put through a short plug of silica gel with 0-10% MeOH/CH2Cl2 to give (1R,2S)-1-[3,5-bis(trifluoromethyl)phenyl]-N2-{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}propane-1,2-diamine. LCMS=619.2 (M+1)+.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d274b97259fc40daa224ef9a814f0c31
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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