Water → HCID 90388277, compound

HRID 2201731Notes

Reaction equation

HRID 2201731 reaction equation
[OH:1][C@@H:2]1[CH2:15][C@H:14]2[C@H:5]([C@H:6]3[C@H:11]([CH2:12][CH2:13]2)[CH2:10][C@:9]2([CH3:20])[C:16](=[O:19])[CH2:17][CH2:18][C@H:8]2[CH2:7]3)[CH2:4][CH2:3]1.[I-].[CH3:22][S+](C)C.CC(C)([O-])C.[K+].O>CS(C)=O>[CH3:20][C@@:9]12[C@:16]3([CH2:22][O:19]3)[CH2:17][CH2:18][C@H:8]1[CH2:7][C@@H:6]1[C@H:11]([CH2:12][CH2:13][C@@H:14]3[C@H:5]1[CH2:4][CH2:3][C@H:2]([OH:1])[CH2:15]3)[CH2:10]2

Participants

6

Reactant 4

HCID 962WaterHCID 75127Trimethylsulfonium iodideHCID 23665647Potassium tert-butoxideHCID 90388282HCID 90388282, compound

Product 1

HCID 90388277HCID 90388277, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of compound 14 (60 mg, 0.23 mmol) in DMSO (3 mL) was added trimethylsulfonium iodide (204 mg, 1.0 mmol) and potassium tert-butoxide (112 mg, 1.0 mmol) at room temperature. After 3 h, water (20 mL) was added and the product 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 15 (48 mg, 72%) as a white solid: 160-162° C.; [α]D20 16.5 (c 0.20, CHCl3); 1H NMR (CDCl3) δ 3.64-3.50 (m, 1H), 2.91 (d, J=4.9 Hz, 1H), 2.62 (d, J=4.9 Hz, 1H), 0.87 (s, 3H); 13C NMR (CDCl3) δ 71.7, 70.6, 53.6, 47.1, 42.0, 40.3, 40.2, 38.9, 38.4, 36.3, 35.7, 31.8, 29.8, 29.6, 28.9 (2×C), 25.8, 25.5, 14.4; IR νmax 3387, 1733 cm−1. Anal. Calcd for (C19H30O2): C, 78.57; H, 10.41. Found: C, 78.36; H, 10.50.

Workup

  1. extractionthe product 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-157fb63736ea4e3889a126dbf0d24937
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

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