(1R*,2R*,4'S*,5R*)-8-Benzyl-4'-(2-benzyloxy-5-trifluoromethoxyphenyl)-6-(tert-butoxycarbonyl)-2',3',4',5'-tetrahydro-1-phenylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan] → (1R*,2R*,4'S*,5R*)-6-(tert-Butoxycarbonyl)-2',3',4',5'-tetrahydro-4'-(2-hydroxy-5-trifluoromethoxyphenyl)-1-phenylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]

HRID 1017280Notes

Reaction equation

HRID 1017280 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:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH2:10][CH:11]2[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])C1C=CC=CC=1>[Pd].C(O)C>[C:42]([O:41][C:39]([CH:11]1[CH2:10][C@:9]2([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[NH:8][C@@H:12]1[CH2:13][CH2:14][C@:15]12[CH2:19][C@@H:18]([C:20]2[CH:25]=[C:24]([O:26][C:27]([F:30])([F:29])[F:28])[CH:23]=[CH:22][C:21]=2[OH:31])[CH2:17][O:16]1)=[O:40])([CH3:45])([CH3:43])[CH3:44]

Participants

4

Reactant 1

HCID 70153496(1R*,2R*,4'S*,5R*)-8-Benzyl-4'-(2-benzyloxy-5-trifluoromethoxyphenyl)-6-(tert-butoxycarbonyl)-2',3',4',5'-tetrahydro-1-phenylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]

Product 1

HCID 70151900(1R*,2R*,4'S*,5R*)-6-(tert-Butoxycarbonyl)-2',3',4',5'-tetrahydro-4'-(2-hydroxy-5-trifluoromethoxyphenyl)-1-phenylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]Yield 114%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (1R*,2R*,4′S*,5R*)-8-benzyl-4′-(2-benzyloxy-5-trifluoromethoxyphenyl)-6-(tert-butoxycarbonyl)-2′,3′,4′,5′-tetrahydro-1-phenylspiro[8-azabicyclo[3.2.1]octane-2,2′-furan] (Description 28; 1.065 g, 1.52 mmol), 10% palladium on charcoal (340 mg, 0.32 mmol) and ethanol (20 ml) was stirred under hydrogen atmosphere (1 atm) at +65° C. for 1.5 hour. 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 (900 mg, 97%).

Workup

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

Sources & evidence

ORD record
ord-2f4bd7fcee89425ab35ccb4bad8212e2
Source dataset
uspto-grants-2002_11
Patent number
US06479486B2

Reaction notes

Loading…