Lithium tri-s-butylborohydride → HCID 11220647, compound

HRID 1696318Notes

Reaction equation

HRID 1696318 reaction equation
[O:1]=[C:2]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@H:3]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:4][CH:5]=[CH2:6].C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+]>C1COCC1>[OH:1][C@H:2]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@H:3]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:4][CH:5]=[CH2:6]

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 86614018HCID 86614018, compound

Product 1

HCID 11220647HCID 11220647, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (R)-benzyl 1-oxo-1-phenylpent-4-en-2-ylcarbamate (2.13 g, 6.89 mmol) in THF (50 mL) at −78° C. under argon was added lithium tri-sec-butylborohydride (20.7 ml, 20.7 mmol). Allowed the mixture to stir for 45 min. Quenched the reaction with saturated aqueous Rochelle's salt (50 mL) and the volatiles were removed in vacuo. The aqueous residue was extracted with ether (3×50 mL). The ether was combined and washed with brine (20 mL), dried over Na2SO4 and filtered. The filtrate was evaporated onto silica gel and purified via flash chromatography (0% to 20%; EtOAc in hexanes). MS m/z=334 [M+Na]+. Calc'd for C19H21NO3: 311.

Workup

  1. customQuenched
  2. customthe reaction with saturated aqueous Rochelle's salt (50 mL)
  3. customthe volatiles were removed in vacuo
  4. extractionThe aqueous residue was extracted with ether (3×50 mL)
  5. washwashed with brine (20 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customThe filtrate was evaporated onto silica gel
  9. custompurified via flash chromatography (0% to 20%; EtOAc in hexanes)

Sources & evidence

ORD record
ord-f72137473ad04259ab7e55abe57f509e
Source dataset
uspto-grants-2012_04
Patent number
US08163766B2

Reaction notes

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