Hydrogen Peroxide → HCID 90388298, compound
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@@H:12]1[CH2:11][CH2:10][C:9](=[O:20])[CH2:8]3)[CH2:3]2.CCC(C)[BH-](C(C)CC)C(C)CC.[K+].[OH-].[Na+].OO>C1COCC1>[OH:20][C@H:9]1[CH2:8][C@H:7]2[C@@H:12]([C@@H:13]3[C@@H:4]([CH2:5][CH2:6]2)[CH2:3][C@@:2]2([CH3:1])[C:18](=[O:19])[CH2:17][CH2:16][C@@H:15]2[CH2:14]3)[CH2:11][CH2:10]1Participants
Procedure
To a solution of compound 38 (570 mg, 2.1 mmoL) in THF (20 mL) was added K-selectride (2.6 mmol, 2.6 mL, 1.0 M in THF) at −78° C. After 3 h, aqueous 10% NaOH (30 mL) and 30% H2O2 (20 mL) were added at −78° C. After addition, the reaction was warmed up to room temperature for 1 h. The product was extracted into EtOAc (50 mL×3), and 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 39 (456 mg, 80%) as a white solid: mp 143-145° C., [α]D25 −41.0 (c 0.19, CHCl3); 1H NMR (CDCl3) δ 3.95-3.90 (m, 1H), 0.75 (s, 3H); 13C NMR (CDCl3) δ 220.8, 65.8, 48.1, 47.5, 46.9, 45.4, 40.2, 39.1, 37.8, 35.8, 35.4, 33.8, 33.7, 32.5, 28.1, 23.8, 23.1, 13.3; IR νmax 3422, 1737 cm−1; Anal. Calcd for (C18H25O2): C, 78.21; H, 10.21. Found: C, 78.29; H, 10.43.
Workup
- additionAfter addition
- extractionThe product was extracted into EtOAc (50 mL×3)
- customthe combined extracts were dried
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash column chromatography (silica gel eluted with 30% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-81a79ae0263448cf8ddc9cc41f39a95d
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365502B2
Reaction notes
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