Lithium tri-s-butylborohydride → HCID 86691846, compound

HRID 1616232Notes

Reaction equation

HRID 1616232 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[C:10](=[N:12]/[S:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])/[CH3:11])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C@H:10]([NH:12][S:13]([C:15]([CH3:16])([CH3:18])[CH3:17])=[O:14])[CH3:11])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

5

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 89735588HCID 89735588, compound

Product 1

HCID 86691846HCID 86691846, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 38-1 (500 mg, 1.5 mmol) in THF (4 mL) at −78 C was added L-Selectride (3.1 mL, 3.1 mmol, 1M). After 10 minutes, the reaction was diluted in EtOAc, washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered and concentrated. Purification by reverse phase chromatography (1-100%, 0.1% TFA in H2O/Acetonitrile) gave desired product. MS (M+H)+: observed=329.0/331.0, calculated=329.3/331.3.

Workup

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by reverse phase chromatography (1-100%, 0.1% TFA in H2O/Acetonitrile)

Sources & evidence

ORD record
ord-50c28bc851004b429d62911ffcb29678
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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