Borane;tetrahydrofuran → tert-Butyl (4-(hydroxymethyl)cyclopent-2-en-1-yl)carbamate

HRID 1838449Notes

Reaction equation

HRID 1838449 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>[OH:15][CH2:14][CH:12]1[CH2:13][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:10]=[CH:11]1

Participants

4

Reactant 2

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

Product 1

HCID 21933810tert-Butyl (4-(hydroxymethyl)cyclopent-2-en-1-yl)carbamateYield 69.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-t-Butoxycarbonylaminocyclopent-2-enecarboxylic acid (1 g, 4.4 mmol) was dissolved in THF (10 mL) and borane-THF (1.5 mL, 1M solution) was added drop-wise at 0° C. and stirred overnight at rt. The reaction mixture was poured into ice-cold water (10 mL) and extracted with ethyl acetate (2×50 mL). The ethyl acetate extract was washed with brine, dried over sodium sulfate, filtered and evaporated to yield N-[4-(hydroxy-methyl)cyclopent-2-enyl](t-butoxy)carboxamide (655 mg, 69%). ESMS: 214 (M+1)+, 236 (M+23)+, 248 (M+35)−, 272 (M+59)−. 1H NMR (CDCl3): δ 1.40 (s, 9H), 2.16 (s, 1H), 2.44-2.52 (m, 2H), 2.82-2.83 (m, 1H), 3.54-3.66 (m, 2H), 5.74-5.81 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. extractionThe ethyl acetate extract
  3. washwas washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-a27d9774b6ac4c619d97fa0926da9f1d
Source dataset
uspto-grants-2004_01
Patent number
US06673809B2

Reaction notes

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