Lawesson's reagent → (1R,2R,5S,6R)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octan-6-thioamide

HRID 2088221Notes

Reaction equation

COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH2:23]([N:30]1[C@@H:35]2[C@H:36]([C:38]([NH2:40])=O)[CH2:37][C@@:31]1([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C@H:32]([O:41][CH2:42][C:43]1[CH:48]=[C:47]([C:49]([F:52])([F:51])[F:50])[CH:46]=[C:45]([C:53]([F:56])([F:55])[F:54])[CH:44]=1)[CH2:33][CH2:34]2)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1(C)C=CC=CC=1>[CH2:23]([N:30]1[C@@H:35]2[C@H:36]([C:38](=[S:10])[NH2:40])[CH2:37][C@@:31]1([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C@H:32]([O:41][CH2:42][C:43]1[CH:48]=[C:47]([C:49]([F:52])([F:51])[F:50])[CH:46]=[C:45]([C:53]([F:56])([F:55])[F:54])[CH:44]=1)[CH2:33][CH2:34]2)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Lawesson's reagent (0.23 g, 0.57 mmol) was added to a solution of (1R*,2R*,5S*,6R*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxyl}-1-phenyl-8-azabicyclo[3.2.1]octan-6-carboxamide (Example 75; 0.64 g, 1.14 mmol) in toluene (20 ml). The mixture was stirred at 100° C. for 1 hour then concentrated in vacuo. The residue was chromatographed on silica gel eluting with 2 and 3% methanol/dichloromethane to yield the title compound (0.162 g, 25%).

Workup

concentrationthen concentrated in vacuo
customThe residue was chromatographed on silica gel eluting with 2 and 3% methanol/dichloromethane

Sources & evidence

ORD record: ord-479c06664a23454b8aabfe271090f82e
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06727249B2

Reaction notes

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