Borane → ethyl 3-(3-hydroxypropyl)-1H-indole-2-carboxylate

HRID 533232Notes

Reaction equation

HRID 533232 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>[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 6331BoraneHCID 612032Ethyl 3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of ethyl 3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate (2.82 g) in THF (40 mL) was added 1M 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-ba6cb44fbc694b65b1b755aec29fca43
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Reaction notes

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