(1R*,2R*,4'S*,5S*,6R*)-8-Benzyl-4'-(2-benzyloxy-5-trifluoromethoxyphenyl)-2',3',4',5'-tetrahydro-1-phenyl-6-phenylsulfonylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan] → (1R*,2R*,4'S*,5S*,6R*)-2',3',4',5'-Tetrahydro-4'-(2-hydroxy-5-trifluoromethoxyphenyl)-1-phenyl-6-phenylsulphonylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]

HRID 1017281Notes

Reaction equation

HRID 1017281 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[CH:25]=[C:24]([O:26][C:27]([F:30])([F:29])[F:28])[CH:23]=[CH:22][C:21]=4[O:31]CC4C=CC=CC=4)[CH2:17][O:16]3)[C@:9]1([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH2:10][C@H:11]2[S:39]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)(=[O:41])=[O:40])C1C=CC=CC=1>[Pd].C(O)C>[OH:31][C:21]1[CH:22]=[CH:23][C:24]([O:26][C:27]([F:30])([F:28])[F:29])=[CH:25][C:20]=1[C@H:18]1[CH2:17][O:16][C@:15]2([CH2:14][CH2:13][C@@H:12]3[NH:8][C@@:9]2([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:10][C@H:11]3[S:39]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)(=[O:41])=[O:40])[CH2:19]1

Participants

4

Reactant 1

HCID 70153087(1R*,2R*,4'S*,5S*,6R*)-8-Benzyl-4'-(2-benzyloxy-5-trifluoromethoxyphenyl)-2',3',4',5'-tetrahydro-1-phenyl-6-phenylsulfonylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]

Product 1

HCID 70152267(1R*,2R*,4'S*,5S*,6R*)-2',3',4',5'-Tetrahydro-4'-(2-hydroxy-5-trifluoromethoxyphenyl)-1-phenyl-6-phenylsulphonylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]Yield 106.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (1R*,2R*,4′S*,5S*,6R*)-8-benzyl-2′,3′,4′,5′-tetrahydro-4′-(2-benzyloxy-5-trifluoromethoxyphenyl)-1-phenyl-6-phenylsulphonylspiro[8-azabicyclo[3.2.1]octane-2,2′-furan](Description 16; 2.2 g, 2.97 mmol), 5% palladium on charcoal (3 g, 1.4 mmol) and ethanol (55 ml) was stirred under hydrogen atmosphere (1 atm) at +70° C. for 70 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 (1.77 g, quant.).

Workup

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

Sources & evidence

ORD record
ord-530c45401c8044a1a4fe7df6116379bd
Source dataset
uspto-grants-2002_11
Patent number
US06479486B2

Reaction notes

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