Trifluoroacetic acid → HCID 86586743, compound

HRID 2088196Notes

Reaction equation

HRID 2088196 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([C:16]([O:18]C(C)(C)C)=[O:17])[CH2:15][C@@:9]1([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C@H:10]([O:23][C@H:24]([C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=1)[CH3:25])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([C:16]([OH:18])=[O:17])[CH2:15][C@@:9]1([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C@H:10]([O:23][C@H:24]([C:26]1[CH:27]=[C:28]([C:36]([F:38])([F:39])[F:37])[CH:29]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:31]=1)[CH3:25])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86586744HCID 86586744, compound

Product 1

HCID 86586743HCID 86586743, compoundYield 161.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1R*,2R*,5S*,6R*)-8-Benzyl-2-{(1S*)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane (Example 128a; 3.28 g, 5.18 mmol) was dissolved in dichloromethane (30 ml) and trifluoroacetic acid added (8 ml) and the reaction mixture stirred overnight at room temperature. The reaction mixture was concentrated in vacuo then triturated with diethyl ether (×3) to give the title compound as a brown solid (4.82 g).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthen triturated with diethyl ether (×3)

Sources & evidence

ORD record
ord-758075df67274bf2a205dba1f8c7e78d
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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