Lithium triethylborohydride → HCID 57974645, compound

HRID 1864686Notes

Reaction equation

HRID 1864686 reaction equation
C[O:2][C:3]([C@@H:5]1[C@H:9]([O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7][N:6]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=O.[Li+].[B-](CC)(CC)CC>C1COCC1>[C:31]([O:30][C:28]([N:6]1[CH2:7][CH2:8][C@@H:9]([O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@H:5]1[CH2:3][OH:2])=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 23712863Lithium triethylborohydrideHCID 57974634HCID 57974634, compound

Product 1

HCID 57974645HCID 57974645, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of compound 1E (538 mg, 1.11 mmol) in THF (10 mL) at −78° C. was added a 1 M solution of Super-Hydride® in THF (5.50 mL, 5.50 mmol). The cold bath was removed and the reaction was allowed to warm to rt. After 3 h, the reaction was poured into a 1-L Erlenmeyer flask and was carefully quenched with ice while stirring and then diluted with EtOAc. The layers were separated and the organic layer was washed with 1 M H3PO4, saturated aqueous NaHCO3 and brine, dried (MgSO4), filtered and concentrated. The residue was purified via flash chromatography (silica gel, 0-40% EtOAc in hexane) to provided the title compound (332 mg).

Workup

  1. customThe cold bath was removed
  2. additionthe reaction was poured into a 1-L Erlenmeyer flask
  3. customwas carefully quenched with ice
  4. additiondiluted with EtOAc
  5. customThe layers were separated
  6. washthe organic layer was washed with 1 M H3PO4, saturated aqueous NaHCO3 and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified via flash chromatography (silica gel, 0-40% EtOAc in hexane)

Sources & evidence

ORD record
ord-4a3420a7b3354434bda11e8b5e39c12e
Source dataset
uspto-grants-2009_12
Patent number
US07625923B2

Reaction notes

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