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 1250151Notes

Reaction equation

HRID 1250151 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>CCO.[Pd]>[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 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 3-(1,4-dioxa-spiro[4.5]dec-7-en-8-yl)-1H-indole (10.0 g, 39.2 mmol) and 10% Pd/C (1.0 g) in 100 mL of EtOH was placed under 40 psi of H2 and shaken at 23° C. for 3 h. The Pd/C was removed via filtration, and the solvent evaporated. Flash chromatography (CH2Cl2/MeOH) gave 8.66 g (33.7 mmol, an 86% yield) of the title compound as a white solid. MS (ES) m/z (relative intensity): 258 (M++H, 100).

Workup

  1. customThe Pd/C was removed via filtration
  2. customthe solvent evaporated
  3. customFlash chromatography (CH2Cl2/MeOH) gave 8.66 g (33.7 mmol

Sources & evidence

ORD record
ord-db35759184c94011a2e94fda82cd50ae
Source dataset
uspto-grants-2002_01
Patent number
US06337326B1

Reaction notes

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