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

HRID 2088206Notes

Reaction equation

HRID 2088206 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH2:7][CH2:8][N:9]1[N:13]=[N:12][C:11]([C@@H:14]2[CH2:20][C@:19]3([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:21]([CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C@H:15]2[CH2:16][CH2:17][C@H:18]3[O:35][CH2:36][C:37]2[CH:42]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:40]=[C:39]([C:47]([F:50])([F:49])[F:48])[CH:38]=2)=[N:10]1.C(N(CC)CC)C>ClCCl>[CH2:22]([N:21]1[C@@H:15]2[C@H:14]([C:11]3[N:12]=[N:13][N:9]([CH2:8][CH2:7][NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[N:10]=3)[CH2:20][C@@:19]1([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C@H:18]([O:35][CH2:36][C:37]1[CH:42]=[C:41]([C:43]([F:44])([F:45])[F:46])[CH:40]=[C:39]([C:47]([F:49])([F:50])[F:48])[CH:38]=1)[CH2:17][CH2:16]2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 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]octane

Product 1

HCID 86586754(1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-{2-[2-(methylsulphonylamino)ethyl]-2H-tetrazol-5-yl}-1-phenyl-8-azabicyclo[3.2.1]octaneYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulphonyl chloride (90 mg, 0.78 mmol) was added to a solution of (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 (Example 141; 0.45 g, 0.71 mmol) and triethylamine (101 mg, 1 mmol) in dichloromethane (10 ml). The reaction mixture was stirred at room temperature for 3 hours then washed with water (×2). The organic layer was separated, dried (MgSO4), filtered and concentrated to yield the title compound (0.47 g, 94%).

Workup

  1. washthen washed with water (×2)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ceb9059853534ad58af146f6680b16c0
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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