2,6-Lutidine → (S)-9-(tert-Butyldimethylsilyloxy)-4-isopropyl-7,7-dimethyl-2',3',5',6,6',7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3-one

HRID 573801Notes

Reaction equation

HRID 573801 reaction equation
[CH:1]([C:4]1[C:13]2[C:14](=[O:22])[O:15][C:16]3([CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[C:12]=2[C:11]2[C@@H:10]([OH:23])[CH2:9][C:8]([CH3:25])([CH3:24])[CH2:7][C:6]=2[N:5]=1)([CH3:3])[CH3:2].N1C(C)=CC=CC=1C.[C:34]([Si:38](OS(C(F)(F)F)(=O)=O)([CH3:40])[CH3:39])([CH3:37])([CH3:36])[CH3:35]>O1CCCC1>[Si:38]([O:23][C@H:10]1[CH2:9][C:8]([CH3:25])([CH3:24])[CH2:7][C:6]2[N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:13]3[C:14](=[O:22])[O:15][C:16]4([CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)[C:12]=3[C:11]1=2)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:40])[CH3:39]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 66761429(S)-4-Isopropyl-9-hydroxy-7,7-dimethyl-2',3',5',6,6',7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3-one

Product 1

HCID 66762310(S)-9-(tert-Butyldimethylsilyloxy)-4-isopropyl-7,7-dimethyl-2',3',5',6,6',7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.2 g (S)-4-Isopropyl-9-hydroxy-7,7-dimethyl-2′,3′,5′,6,6′,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4′-pyran]-3-one are dissolved in 15 ml tetrahydrofurane and 1.31 ml 2,6-lutidine and 2.44 ml trifluoromethanesulfonic acid-tert.-butyldimethylsilylester are added dropwise and the mixture is stirred for 4 hours at room temperature. Then the reaction is absorbed onto silica gel and chromatographed on silica gel (petrole ether/ethylacetate 100:0 to 50:50).

Workup

  1. customThen the reaction is absorbed onto silica gel
  2. customchromatographed on silica gel (petrole ether/ethylacetate 100:0 to 50:50)

Sources & evidence

ORD record
ord-e8e044ddc2454f7fb2ecfbc97d6ac777
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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