Hydrogen Peroxide → HCID 78323392, compound

HRID 2201734Notes

Reaction equation

HRID 2201734 reaction equation
[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[CH2:14][C@@H:13]1[C@H:4]([CH2:5][CH2:6][C@H:7]3[C@@:12]1([CH3:20])[CH2:11][CH2:10][C:9](=[O:21])[CH2:8]3)[CH2:3]2.CCC(C)[BH-](C(C)CC)C(C)CC.[K+].[OH-].[Na+].OO>C1COCC1>[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[CH2:14][C@@H:13]1[C@H:4]([CH2:5][CH2:6][C@H:7]3[C@@:12]1([CH3:20])[CH2:11][CH2:10][C@H:9]([OH:21])[CH2:8]3)[CH2:3]2

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 90388246HCID 90388246, compound

Product 1

HCID 78323392HCID 78323392, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 21 (460 mg, 1.6 mmoL) in THF (20 mL) was added K-selectride (2.0 mmol, 2.0 mL, 1.0 M) at −78° C. After 3 h, 10% aqueous NaOH (30 mL) and 30% H2O2 (20 mL) were added at −78° C. The reaction was then warmed to room temperature for 1 h. The product was extracted into EtOAc (50 mL×3). The combined extracts were dried, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel eluted with 30% EtOAc in hexanes) to give compound 22 (294 mg, 64%) as a white solid: mp 179-181° C., [α]D25 +46.9 (c 0.16, CHCl3); 1H NMR (CDCl3) δ 4.05 (s, br, 1H), 0.85 (s, 3H), 0.79 (s, 3H); 13C NMR (CDCl3) δ 221.1, 66.4, 54.6, 47.8, 45.8, 39.8, 39.1, 36.4, 35.7, 34.8, 32.0, 31.8, 28.8, 28.7, 24.1, 24.0, 13.6, 11.2; IR νmax 3434, 1736 cm−1. Anal. Calcd for (C19H30O2): C, 78.57; H, 10.41. Found: C, 78.45; H, 10.28.

Workup

  1. extractionThe product was extracted into EtOAc (50 mL×3)
  2. customThe combined extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (silica gel eluted with 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-04de60df9ec543d09b3f780f77fcff7d
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

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