3-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)-1H-indole → 3-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-indole

HRID 992011Notes

Reaction equation

HRID 992011 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[NH:13][CH:12]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1>[Pd].C(O)C>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[NH:13][CH:12]=3)[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 27638573-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)-1H-indole

Product 1

HCID 108487533-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-indoleYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(1,4-dioxa-spiro[4,5]dec-7-en-8-yl)-1H-indole (8.0 g, 31.3 mmol) and 10% palladium on carbon (1.3 g) in ethanol (700 ml) was hydrogenated for 18 hours. The catalyst was filtered off and the solvent removed under vacuum to afford 8.01 g (99%) of product as a white solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-474e5745863b47ef91f260313b377801
Source dataset
uspto-grants-2002_10
Patent number
US06465482B2

Reaction notes

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