Lithium borohydride → HCID 67274069, compound

HRID 1020914Notes

Reaction equation

HRID 1020914 reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[C:10]([C:16]1[CH2:20][CH2:19][CH2:18][CH:17]=1)[NH:11]2)C.[Li+].[BH4-]>C1COCC1>[C:16]1([C:10]2[NH:11][C:12]3[C:8]([CH:9]=2)=[C:7]([O:6][CH2:5][CH2:4][OH:3])[CH:15]=[CH:14][CH:13]=3)[CH2:20][CH2:19][CH2:18][CH:17]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 67273858HCID 67273858, compound

Product 1

HCID 67274069HCID 67274069, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 216 mg (0.758 mmol) of the ester from step 1 in 5 mL THF at 0° C. was added 455 μL (0.91 mmol, 1.2 eq) of LiBH4 solution (1M THF) and the reaction was stirred at room temperature overnight. The reaction was quenched with 1N HCl, extracted with EtOAc, washed with H2O, aqueous NaCl solution, dried (Mg SO4), and concentrated in vacuo to yield 167 mg (91%) of 2-(2-cyclopent-1-enyl-1H-indol-4-yloxy)-ethanol.

Workup

  1. customThe reaction was quenched with 1N HCl
  2. extractionextracted with EtOAc
  3. washwashed with H2O, aqueous NaCl solution
  4. dry with materialdried (Mg SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-620cbd4f0456439895ee25d78d25e7c9
Source dataset
uspto-grants-2014_05
Patent number
US08716493B2

Reaction notes

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