Lithium tri-s-butylborohydride → HCID 66661829, compound

HRID 557917Notes

Reaction equation

HRID 557917 reaction equation
[O:1]=[C:2]1[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][N:4]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:3]1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>O1CCCC1>[OH:1][CH:2]1[CH:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:5][N:4]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:3]1

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 66662325HCID 66662325, compound

Product 1

HCID 66661829HCID 66661829, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of benzyl 3-oxo-4-phenylpyrrolidine-1-carboxylate (200 mg, 0.0007 mol) in tetrahydrofuran (2.0 mL, 0.025 mol) under a N2 atmosphere at −78° C. was added L-Selectride® in tetrahydrofuran (1M, 4.1 mL) with stirring. The mixture was stirred at this temperature for 1.5 hours. LCMS indicated that the starting material was consumed and the reaction was quenched with water. The solution was adjusted to pH ˜6 to 7 and was extracted with EtOAc. The organic extract was washed with brine, dried over Na2SO4, filtered and the filtrate was concentrated. The resulting residue was purified with Combiflash, eluting with EtOAc/hexane to afford the product (125 mg). LCMS: m/z 298.0 (M+H+); 320.0 (M+Na+).

Workup

  1. stirringThe mixture was stirred at this temperature for 1.5 hours
  2. customwas consumed
  3. customthe reaction was quenched with water
  4. extractionwas extracted with EtOAc
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated
  10. customThe resulting residue was purified with Combiflash
  11. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-210e81e0794447b1b1998fe068fd5ad9
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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