Ethyl 3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate → ethyl 3-(3-hydroxypropyl)-1H-indole-2-carboxylate

HRID 1013272Notes

Reaction equation

HRID 1013272 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])C.B.C1COCC1>C1COCC1>[OH:3][CH2:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 612032Ethyl 3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylateHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 67316234ethyl 3-(3-hydroxypropyl)-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate (2.82 g) in THF (40 mL) was added IM borane-THF (40 mL). The mixture was stirred at room temperature for 16 hours, quenched with methanol (100 mL) and concentrated. The concentrate was purified by flash column chromatography on silica gel with 5-25% ethyl acetate/hexanes.

Workup

  1. customquenched with methanol (100 mL)
  2. concentrationconcentrated
  3. customThe concentrate was purified by flash column chromatography on silica gel with 5-25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-10a0382ed8b54d5796c9f3d1eccf01e0
Source dataset
uspto-grants-2011_07
Patent number
US07981888B2

Reaction notes

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