1-tert-Butyl 6-methyl 1H-indole-1,6-dicarboxylate → tert-Butyl 6-(hydroxymethyl)-1H-indole-1-carboxylate

HRID 1774208Notes

Reaction equation

HRID 1774208 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[N:11]1([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20](OC)=[O:21])[CH:18]=2)[CH:13]=[CH:12]1>C1(C)C=CC=CC=1>[OH:21][CH2:20][C:17]1[CH:18]=[C:19]2[C:14]([CH:13]=[CH:12][N:11]2[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 208216591-tert-Butyl 6-methyl 1H-indole-1,6-dicarboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 23560816tert-Butyl 6-(hydroxymethyl)-1H-indole-1-carboxylateYield 65.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-50 °C

Procedure

Diisobutylaluminum hydride (1M in toluene, 12 mL, 12 mmol) was added to a solution of 1-tert-butyl 6-methyl 1H-indole-1,6-dicarboxylate (1.38 g, 5.00 mmol) in toluene (15 mL) at −50° C. over 10 minutes. After being stirred at −50° C. for 30 minutes, the reaction was quenched with methanol (2.5 mL) and water (2.5 mL). The resulting precipitate was filtered off, and the filtrate was evaporated. The residue was purified by silica gel chromatography, eluting with petroleum ether/ethyl acetate (5:1 to 1:1) to afford tert-butyl 6-(hydroxymethyl)-1H-indole-1-carboxylate (815 mg, 55% yield) as an oil. LCMS (ESI) m/z 174.3 [M+H-18-56]+, 230.3 [M+H-18]+.

Workup

  1. customthe reaction was quenched with methanol (2.5 mL) and water (2.5 mL)
  2. filtrationThe resulting precipitate was filtered off
  3. customthe filtrate was evaporated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with petroleum ether/ethyl acetate (5:1 to 1:1)

Sources & evidence

ORD record
ord-b0d148de6211498683d1556c70858187
Source dataset
uspto-grants-2016_02
Patent number
US09259470B2

Reaction notes

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