(1R*,2R*,4'S*,5R*)-8-Benzyl-2',3',4',5'-tetrahydro-4'-[(2RS)-2,3-dihydro-2-methyl-5-trifluoromethoxybenzofuran-7-yl]-1-phenyl-6-phenylsulphonylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan] → (1R*,2R*,4'S*,5R*)-2',3',4',5'-Tetrahydro-4'-[(2RS)-2,3-dihydro-2-methyl-5-trifluoromethoxybenzofuran-7-yl]-1-phenyl-6-phenylsulphonylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]

HRID 1017284Notes

Reaction equation

HRID 1017284 reaction equation
C([N:8]1[C@@H:12]2[CH2:13][CH2:14][C@@:15]3([CH2:19][C@@H:18]([C:20]4[C:28]5[O:27][CH:26]([CH3:29])[CH2:25][C:24]=5[CH:23]=[C:22]([O:30][C:31]([F:34])([F:33])[F:32])[CH:21]=4)[CH2:17][O:16]3)[C@:9]1([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH2:10][CH:11]2[S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:37])=[O:36])C1C=CC=CC=1>[Pd].C(O)C>[CH3:29][CH:26]1[CH2:25][C:24]2[CH:23]=[C:22]([O:30][C:31]([F:34])([F:32])[F:33])[CH:21]=[C:20]([C@H:18]3[CH2:17][O:16][C@:15]4([CH2:14][CH2:13][C@H:12]5[NH:8][C@@:9]4([C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)[CH2:10][CH:11]5[S:35]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)(=[O:36])=[O:37])[CH2:19]3)[C:28]=2[O:27]1

Participants

4

Reactant 1

HCID 70152365(1R*,2R*,4'S*,5R*)-8-Benzyl-2',3',4',5'-tetrahydro-4'-[(2RS)-2,3-dihydro-2-methyl-5-trifluoromethoxybenzofuran-7-yl]-1-phenyl-6-phenylsulphonylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]

Product 1

HCID 70152459(1R*,2R*,4'S*,5R*)-2',3',4',5'-Tetrahydro-4'-[(2RS)-2,3-dihydro-2-methyl-5-trifluoromethoxybenzofuran-7-yl]-1-phenyl-6-phenylsulphonylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]Yield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (1R*,2R*,4S*,5R*)-8-benzyl-2′,3′,4′,5′-tetrahydro-4′-[(2RS)-2,3-dihydro-2-methyl-5-trifluoromethoxybenzofuran-7-yl]-1-phenyl-6-phenylsulphonylspiro[8-azabicyclo[3.2.1]octane-2,2′-furan] (Example 7; 200 mg, 0.29 mmol), 10% palladium on charcoal (375 mg, 0.35 mmol) and ethanol (25 ml) was stirred under hydrogen atmosphere (1 atm) at +70° C. for 30 minutes. The reaction mixture was cooled to room temperature, flushed with nitrogen gas and filtered through a pad of Celite™. The filtrate was concentrated to give the title compound (160 mg, 92%).

Workup

  1. customflushed with nitrogen gas
  2. filtrationfiltered through a pad of Celite™
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-551d61360a284a3a8b97da7e3c8866c9
Source dataset
uspto-grants-2002_11
Patent number
US06479486B2

Reaction notes

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