Tetrahydrofuran → HCID 70155508, compound

HRID 2187039Notes

Reaction equation

HRID 2187039 reaction equation
CO[CH:3]([C:19](O)=[O:20])[CH2:4][CH2:5][C@@:6]12[CH2:17][CH2:16][CH2:15][C:13]3[C:14]1=[C:9]([CH:10]=[CH:11][CH:12]=3)[NH:8][C:7]2=[O:18].O1CCCC1.[BH4-].[Li+]>C(COC)OC>[OH:20][CH2:19][CH2:3][CH2:4][CH2:5][C@@:6]12[CH2:17][CH2:16][CH2:15][C:13]3[C:14]1=[C:9]([CH:10]=[CH:11][CH:12]=3)[NH:8][C:7]2=[O:18]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 70155057HCID 70155057, compound

Product 1

HCID 70155508HCID 70155508, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

(S)-2a-(3-methoxycarboxypropyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (4.1 g, 15 mmol) was dissolved in dimethoxyethane (60 ml). Then, tetrahydrofuran solution of 1.6 M lithiumborohydride (9.0 ml, 18 mmol) was added to the resulting solution and stirred at room temperature for two days. The solvent was evaporated from the reaction mixture, and ethyl acetate, water and hydrochloric acid (1N) were added to the resulting residue. The reaction product was extracted with ethyl acetate, and the extracted product was washed with saturated saline solution, successively dried over anhydrous sodium sulfate, followed by evaporating the solvent. The resulting product was separated and purified by means of silica gel column chromatography, whereby 2.15 g (yield 58%) of the above-described object compound could be obtained.

Workup

  1. customThe solvent was evaporated from the reaction mixture, and ethyl acetate, water and hydrochloric acid (1N)
  2. additionwere added to the resulting residue
  3. extractionThe reaction product was extracted with ethyl acetate
  4. washthe extracted product was washed with saturated saline solution
  5. dry with materialsuccessively dried over anhydrous sodium sulfate
  6. customby evaporating the solvent
  7. customThe resulting product was separated

Sources & evidence

ORD record
ord-06050b74c32449c69a0a50ae202f2746
Source dataset
uspto-grants-2002_06
Patent number
US06407112B1

Reaction notes

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