Borane;tetrahydrofuran → HCID 18453470, compound

HRID 352179Notes

Reaction equation

HRID 352179 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH:12]([C:14](O)=[O:15])[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B.C1COCC1>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:13][C@@H:12]([CH2:14][OH:15])[CH:11]=[CH:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 27344894-((Tert-butoxycarbonyl)amino)cyclopent-2-ene-1-carboxylic acid

Product 1

HCID 18453470HCID 18453470, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-t-butoxycarbonylaminocyclopent-2-enecarboxylic acid (1 g, 4.4 mmol) dissolved in THF (100 ml) and added with borane-THF (4.5 ml, 4.5 mmol) at 0° C. and stirred overnight at r.t. The reaction mixture was poured into ice-cold water (100 ml) and extracted with ethyl acetate. The ethyl acetate extract was washed with brine, dried over sodium sulfate and evaporated to obtain the title compound (655 mg, 69%). ESMS: 214 (M+1)+, 236 (M+23)+, 248 (M+35)−, 272 (M+59)−.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-a2a96858319743bcb968891f3d327980
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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