HCID 12979375, compound → HCID 12979373, compound

HRID 2097175Notes

Reaction equation

HRID 2097175 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:12](OCC)=[O:13].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]1[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[CH2:12][OH:13]

Participants

4

Reactant 2

HCID 12979375HCID 12979375, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12979373HCID 12979373, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 3,7-dimethyl-1H-indole-2-carboxylate (1.84 g, 8.4 mmol) in THF (20 mL) was added to an ice-cooled solution of 1.0 M LAH in THF (17.8 mL 17.8 mmol) and stirred overnight. The reaction was quenched with ethyl acetate (5 mL) and 15% aqueous sodium hydroxide (5 mL), filtered through celite and evaporated in vacuo. The crude reaction was chromatographed over silica gel eluting with methanol/dichloromethane (1%) to afford the title compound (440 mg, 30%). 1H NMR (400 MHz, CDCl3) δ 8.39 (s, 1H), 7.39 (d, J=7.7 Hz, 1H), 7.06 (t, J=7.2 Hz, 1H), 6.99 (d, J=7.1 Hz, 1H), 4.82 (s, 2H), 4.11 (q, J=7.1 Hz, 2H), 2.45 (s, 3H), 2.28 (s, 3H), 1.26 (t, J=7.1 Hz, 3H).

Workup

  1. customThe reaction was quenched with ethyl acetate (5 mL) and 15% aqueous sodium hydroxide (5 mL)
  2. filtrationfiltered through celite
  3. customevaporated in vacuo
  4. customThe crude reaction
  5. customwas chromatographed over silica gel eluting with methanol/dichloromethane (1%)

Sources & evidence

ORD record
ord-02566b61c8ec441ab9a8a54606c8c6e6
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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