Lithium borohydride → [1-(Propan-2-yl)-1H-indol-6-yl]methanol

HRID 1510130Notes

Reaction equation

HRID 1510130 reaction equation
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13](OC)=[O:14])[CH:11]=2)[CH:6]=[CH:5]1)([CH3:3])[CH3:2].[BH4-].[Li+]>C1COCC1>[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:13][OH:14])[CH:11]=2)[CH:6]=[CH:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 10608809Methyl 1-isopropyl-1H-indole-6-carboxylate

Product 1

HCID 29038143[1-(Propan-2-yl)-1H-indol-6-yl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. solution of methyl 1-isopropyl-1H-indole-6-carboxylate (0.50 g, 2.30 mmol) in THF (5 mL) was added 1M lithium borohydride in THF (6.90 mL, 6.90 mmol). After stirring at rt for 96 h, quenched with MeOH and let stir for 1 h. The reaction mixture was concentrated, partitioned between saturated sodium bicarbonate and EtOAc, washed with H2O and brine, dried with Na2SO4, and concentrated. The crude compound was chromatographed to give the desired product.

Workup

  1. customquenched with MeOH
  2. stirringlet stir for 1 h
  3. concentrationThe reaction mixture was concentrated
  4. custompartitioned between saturated sodium bicarbonate and EtOAc
  5. washwashed with H2O and brine
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated
  8. customThe crude compound was chromatographed

Sources & evidence

ORD record
ord-8b2dc08af4b54059a33313d5c61c1fd7
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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