Tetrahydrofuran ethanol → 3-(1,4-Dioxa-spiro[4,5]dec-8-yl)-5-cyano-1-methyl-indole

HRID 1872834Notes

Reaction equation

HRID 1872834 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=1)#[N:2].[CH2:19]([OH:21])[CH3:20].[O:22]1CCCC1>[Pd]>[CH2:20]1[O:22][C:16]2([CH2:17][CH2:18][CH:13]([C:6]3[C:5]4[C:9](=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[CH:4]=4)[N:8]([CH3:12])[CH:7]=3)[CH2:14][CH2:15]2)[O:21][CH2:19]1

Participants

4

Reactant 2

HCID 21873804Tetrahydrofuran ethanolHCID 701064644-(5-Cyano-1-methyl-3-indolyl)-cyclohex-3-en

Product 1

HCID 184140773-(1,4-Dioxa-spiro[4,5]dec-8-yl)-5-cyano-1-methyl-indole

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 4-(5-cyano-1-methyl-3-indolyl)-cyclohex-3-en-isomer ethylene ketal (3.77 g) and 10% palladium on carbon (0.99 g) in ethanol-tetrahydrofuran (200:80 ml) was hydrogenated for 5 hours. The catalyst was filtered off and the solvent was removed under vacuum to afford a white powder which was washed with ethanol-hexanes (1:1) and dried under vacuum for 4 hours (2.75 g): mp 170-172° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed under vacuum
  3. customto afford a white powder which
  4. washwas washed with ethanol-hexanes (1:1)
  5. customdried under vacuum for 4 hours (2.75 g)

Sources & evidence

ORD record
ord-adf6d0e2ba8642c6ad79d15608e20312
Source dataset
uspto-grants-2000_08
Patent number
US06110956

Reaction notes

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