Water → (RS)-(5-methoxy-2,3-dihydro-1H-indol-2-yl)-methanol

HRID 278442Notes

Reaction equation

HRID 278442 reaction equation
C[O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH3:15])[CH:11]=2)[NH:6]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[CH3:15][O:14][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[NH:6][CH:5]([CH2:3][OH:2])[CH2:13]2

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 54121458(RS)-5-methoxy-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester

Product 1

HCID 22628355(RS)-(5-methoxy-2,3-dihydro-1H-indol-2-yl)-methanolYield 65.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(RS)-5-methoxy-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester (2.5 g, 12.06 mmol) in THF (130 ml) was added dropwise to a suspension of LiAlH4 in THF (80 ml) at 4° C., and the mixture allowed to stir at RT overnight, and then heated at 65° C. for 4 hr. After cooling, H2O (20 ml) was added cautiously and the mixture stirred 20 min, then filtered and the filtrate extracted with EtOAc (3×50 ml), the extracts were washed with satd. NaCl solution (50 ml), dried (Na2SO4) filtered and evaporated. The crude oil was chromatographed over SiO2 (Merck 230-400 mesh) eluting with CH2Cl2—MeOH (9:1) affording (RS)-(5-methoxy-2,3-dihydro-1H-indol-2-yl)-methanol as a yellow oil (1.41 g, 7.86 mmol, 65%), MS: m/e=179.1 (M+).

Workup

  1. temperatureheated at 65° C. for 4 hr
  2. temperatureAfter cooling
  3. stirringthe mixture stirred 20 min
  4. filtrationfiltered
  5. extractionthe filtrate extracted with EtOAc (3×50 ml)
  6. washthe extracts were washed with satd
  7. dry with materialNaCl solution (50 ml), dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe crude oil was chromatographed over SiO2 (Merck 230-400 mesh)
  11. washeluting with CH2Cl2—MeOH (9:1)

Sources & evidence

ORD record
ord-dedb97ce701043ca8644b26a2bbf1b5f
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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