3-(1,4-Dioxa-spiro[4,5]dec-7-en-8-yl)-2-methyl-1h-indole → 3-(1,4-dioxa-spiro[4,5]dec-8-yl)-2-methyl-1H-indole

HRID 428496Notes

Reaction equation

HRID 428496 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][C:12]=3[CH3:20])=[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][C:12]=3[CH3:20])[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 184141363-(1,4-Dioxa-spiro[4,5]dec-7-en-8-yl)-2-methyl-1h-indole

Product 1

HCID 184140993-(1,4-dioxa-spiro[4,5]dec-8-yl)-2-methyl-1H-indoleYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(1,4-dioxa-spiro[4,5]dec-7-en-8-yl)-2-methyl-1H-indole (2.39 g, 8.9 mmol) and 10% palladium on carbon (0.35 g) in ethanol (80 ml) was hydrogenated for 3 hours. The catalyst was filtered off and then a solution of methylene-methanol (80 ml) was used to dissolve any solids within the celite. The solvent removed under vacuum to afford 2.34 g (97%) of product as an off-white solid, which was triturated with ethyl ether (40 ml) to afford a white solid: mp 166-168° C. The mother liquor was concentrated to afford another 1.2 g of product as a yellow solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. dissolutionto dissolve any solids within the celite
  3. customThe solvent removed under vacuum

Sources & evidence

ORD record
ord-2f7d93ed53e2448ba700903319a147cc
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Reaction notes

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