Tetrahydrofuran → 2,3-dihydro-1H-indol-2-ylmethanol

HRID 1168498Notes

Reaction equation

HRID 1168498 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10](O)=[O:11].C1COCC1>O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 86074Indoline-2-carboxylic acid

Product 1

HCID 27946642,3-dihydro-1H-indol-2-ylmethanolYield 94.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A slurry of racemic indoline-2-carboxylic acid (5.00 g) and anhydrous THF (60 mL) is cooled to 0° C. under an atmosphere of nitrogen. To this slurry is added 1.0 M borane-THF complex (100 mL) via syringe over 40 minutes. The resulting solution is allowed to warm to room temperature while stirring overnight. Water (ca. 400 mL) is slowly added to quench the reaction. The mixture is extracted with diethyl ether (400 mL). The combined organic layers are washed with saturated sodium bicarbonate solution followed by brine, dried (Na2SO4), filtered, and concentrated to afford 4.31 g (94%) of the title compound as a colorless foam. Physical characteristics: MS (ESI+) m/z 150 (M+H)+.

Workup

  1. additionTo this slurry is added 1.0 M borane-THF complex (100 mL) via syringe over 40 minutes
  2. customto quench
  3. customthe reaction
  4. extractionThe mixture is extracted with diethyl ether (400 mL)
  5. washThe combined organic layers are washed with saturated sodium bicarbonate solution
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-826ad71113054876bdb07b4d44a886c0
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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