Lithium tri-s-butylborohydride → HCID 57987368, compound

HRID 1942291Notes

Reaction equation

HRID 1942291 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][C@@H:5]1[C:10](=[O:11])[CH:9]=[CH:8][N:7]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[C@H:6]1[C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>C1COCC1>[CH3:1][O:2][C:3](=[O:32])[CH2:4][C@@H:5]1[C:10](=[O:11])[CH2:9][CH2:8][N:7]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[C@H:6]1[C:22]1[CH:23]=[CH:24][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 57987338HCID 57987338, compound

Product 1

HCID 57987368HCID 57987368, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the enone from Step 2 (1.650 g, 3.7 mmol) in dry THF (40 ml) was cooled to −78° C. and L-selectride® (1.0M in THF, 4.6 ml, 4.6 mmol) was added. The reaction was stirred for 2 mins then quenched with saturated NH4Cl solution. The mixture extracted with EtOAc (×3), the combined extracts were washed with brine, dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (silica, 40-50% Et2O/hexanes) to give the ketone (1.473 g, 89%). 1H NMR (360 MHz, CDCl3) δ: 2.24 (1H, dd, J 4.9, 16.8), 2.57-2.70 (3H, m), 3.46-3.52 (1H, m), 3.58 (3H, s), 3.80-3.89 (1H, m), 4.57 (1H, dd, J 5.2, 14.2), 4.93-4.98 (2H, m), 5.10 (1H, d, J 12.1), 7.07 (2H, s), 7.26-7.41 (5H, m), 7.57 (2H, d, J 8.1).

Workup

  1. customthen quenched with saturated NH4Cl solution
  2. extractionThe mixture extracted with EtOAc (×3)
  3. washthe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography (silica, 40-50% Et2O/hexanes)

Sources & evidence

ORD record
ord-38e6e40493fe4b19880f09488d8300e2
Source dataset
uspto-grants-2013_03
Patent number
US08389547B2

Reaction notes

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