Borane;tetrahydrofuran → HCID 20737787, compound

HRID 354464Notes

Reaction equation

HRID 354464 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10][C@H:9]1[C:17](O)=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].B.C1COCC1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10][C@H:9]1[CH2:17][OH:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 17040146HCID 17040146, compound

Product 1

HCID 20737787HCID 20737787, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of [1-tert-butoxycarbonyl-(2S)-octahydroindolyl]carboxylic acid (1.0 g, 3.7 mmol) in THF (10.0 ml) was added BH3.THF (1.0 M in THF, 8.0 ml) at 0° C. After stirred at room temperature for 1.0 h, the reaction mixture was heated under reflux for 1.5 hr. After cooled, the mixture was concentrated in vacuo. Water was added thereto at 0° C., and extracted with EtOAc. The extract was washed with water, then dried over Na2SO4, and concentrated in vacuo to give [1-tert-butoxycarbonyl-(2S)-octahydroindolyl]methanol (947 mg, quant) as a a colorless oil.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 1.5 hr
  3. temperatureAfter cooled
  4. concentrationthe mixture was concentrated in vacuo
  5. additionWater was added
  6. extractionat 0° C., and extracted with EtOAc
  7. washThe extract was washed with water
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f9fe55e859284fd9b71f8a4f216a831d
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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