Lithium borohydride → HCID 22225487, compound

HRID 2223233Notes

Reaction equation

HRID 2223233 reaction equation
[CH2:1]([O:8][NH:9][C:10]([CH:12]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:13](OCC)=[O:14])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[BH4-]>C1COCC1>[CH2:1]([O:8][NH:9][C:10](=[O:11])[CH:12]([CH2:13][OH:14])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86608445HCID 86608445, compound

Product 1

HCID 22225487HCID 22225487, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-benzyloxycarbamoylheptanoic acid, ethyl ester (12.29 g, 39.98 mmol) in THF (400 mL)) was added LiBH4 (8.70 g, 399.8 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight. Ice-water (500 mL) was then added to the reaction mixture (warning: vigorous evolution of gas). The aqueous layer was extracted with EtOAc (400 mL×2). The organic extracts were washed with water, brine, and dried over MgSO4. After removing the solvent under reduced pressure, flash column chromatography (hexane:EtOAc 1/2) yielded 5.36 g (51%) of the title compound. 1H NMR (400 MHz, CHCl) δ 9.22 (br s, 1H), 7.41–7.28 (m, 5H), 4.89 (q, J=10.6 Hz, 2H), 3.70–3.37 (m, 3H), 2.17 (m, 1H). 1.54 (br s, 1H), 1.27 (m, 6H), 0.88 (t, J=6.9 Hz). MH+ 266.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (400 mL×2)
  2. washThe organic extracts were washed with water, brine
  3. dry with materialdried over MgSO4
  4. customAfter removing the solvent under reduced pressure, flash column chromatography (hexane:EtOAc 1/2)

Sources & evidence

ORD record
ord-67850a24da9a433ea46234922ca49519
Source dataset
uspto-grants-2008_05
Patent number
US07375120B2

Reaction notes

Loading…