(3R,9S)-9-(tert-butyldimethylsilyloxy)-7,7-dimethyl-4-(1-methylcyclopropyl)-3-(4-(trifluoromethyl)phenyl)-2',3',5',6,6',7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran] → (3R,9S)-4-tert-Butyl-9-(tert-butyldimethylsilyloxy)-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2',3',5',6,6',7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]

HRID 573785Notes

Reaction equation

HRID 573785 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([C:21]3([CH3:24])[CH2:23][CH2:22]3)[C:12]3[C@@H:25]([C:33]4[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=4)[O:26][C:27]4([CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[C:11]=3[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(O)(=O)C.C(OC(=O)C)(=O)C.[Pt](=O)=O>[C:21]([C:13]1[C:12]2[C@@H:25]([C:33]3[CH:34]=[CH:35][C:36]([C:39]([F:41])([F:40])[F:42])=[CH:37][CH:38]=3)[O:26][C:27]3([CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[C:11]=2[C:10]2[C@@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]=2[N:14]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 1

HCID 66761645(3R,9S)-9-(tert-butyldimethylsilyloxy)-7,7-dimethyl-4-(1-methylcyclopropyl)-3-(4-(trifluoromethyl)phenyl)-2',3',5',6,6',7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]

Product 1

HCID 66762167(3R,9S)-4-tert-Butyl-9-(tert-butyldimethylsilyloxy)-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2',3',5',6,6',7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

30 mg (3R,9S)-9-(tert-butyldimethylsilyloxy)-7,7-dimethyl-4-(1-methylcyclopropyl)-3-(4-(trifluoromethyl)phenyl)-2′,3′,5′,6,6′,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4′-pyran] are dissolved in 3 ml acetic acid and 1 ml acetic acid anhydride. 30 mg Platinum-(IV)-oxide are added and the mixture is hydrogenated for 2 hours at 60° C. and 3 bar. The catalyst is filtered off and washed with methanol. The liquid phases are combined and the solvents are evaporated in vacuo. The residue is chromatographed on silica gel (petrole ether/ethylacetate 100:0 to 90:10).

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with methanol
  3. customthe solvents are evaporated in vacuo
  4. customThe residue is chromatographed on silica gel (petrole ether/ethylacetate 100:0 to 90:10)

Sources & evidence

ORD record
ord-8d784cfeadd74f34810bd5c120429c06
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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