(1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy)-6-{2-[2-(t-butoxycarbonylamino)ethyl]-2H-tetrazol-5-yl}-1-phenyl-8-azabicyclo[3.2.1]octane → (1R*,2R*,5S*,6R*)-6-[2-(2-Aminoethyl)-2H-tetrazol-5-yl]-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octane

HRID 2088205Notes

Reaction equation

HRID 2088205 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([C:16]3[N:17]=[N:18][N:19]([CH2:21][CH2:22][NH:23]C(OC(C)(C)C)=O)[N:20]=3)[CH2:15][C@@:9]1([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C@H:10]([O:31][CH2:32][C:33]1[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[C:35]([C:43]([F:46])([F:45])[F:44])[CH:34]=1)[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>[NH2:23][CH2:22][CH2:21][N:19]1[N:18]=[N:17][C:16]([C@@H:14]2[CH2:15][C@:9]3([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C@H:13]2[CH2:12][CH2:11][C@H:10]3[O:31][CH2:32][C:33]2[CH:34]=[C:35]([C:43]([F:44])([F:45])[F:46])[CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=2)=[N:20]1

Participants

3

Reactant 1

HCID 86586752(1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy)-6-{2-[2-(t-butoxycarbonylamino)ethyl]-2H-tetrazol-5-yl}-1-phenyl-8-azabicyclo[3.2.1]octane

Product 1

HCID 86586753(1R*,2R*,5S*,6R*)-6-[2-(2-Aminoethyl)-2H-tetrazol-5-yl]-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octaneYield 96.6%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

(1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-{2-[2-(t-butoxycarbonylamino)ethyl]-2H-tetrazol-5-yl}-1-phenyl-8-azabicyclo[3.2.1 ]octane (Example 140; 0.54 g) was stirred in 20% trifluoroacetic acid/dichloromethane for 90 minutes. The mixture was concentrated in vacuo. The residue was partitioned between saturated sodium carbonate and dichloromethane. The organic layer was separated, dried (MgSO4), filtered and concentrated to yield the title compound (0.45 g, 96%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was partitioned between saturated sodium carbonate and dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-347ca33897d143d5b63a4c742bd0dd83
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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