Water → HCID 78323393, compound

HRID 2201735Notes

Reaction equation

HRID 2201735 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@H:9]([OH:21])[CH2:8]3)[CH2:3]2.[I-].[CH3:23][S+](C)C.CC(C)([O-])C.[K+].O>CS(C)=O>[CH3:1][C@@:2]12[C@:18]3([CH2:23][O:19]3)[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 962WaterHCID 75127Trimethylsulfonium iodideHCID 23665647Potassium tert-butoxideHCID 78323392HCID 78323392, compound

Product 1

HCID 78323393HCID 78323393, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of compound 22 (35 mg, 0.12 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 20% EtOAc in hexanes) to afford compound 23 (23 mg, 63%): mp 138-140° C.; [α]D20 −16.7 (c 0.15, CHCl3); 1H NMR (CDCl3) δ 4.06 (s, br, 1H), 2.90 (d, J=5.1 Hz, 1H), 2.61 (d, J=5.1 Hz, 1H), 0.86 (s, 3H), 0.79 (s, 3H); 13C NMR (CDCl3) δ 70.5, 66.6, 54.6, 53.6, 47.1, 42.6, 40.2, 39.2, 36.4, 35.8, 35.1, 32.0, 31.8, 29.1, 28.9, 28.8, 25.9, 24.4, 14.4, 11.2; IR νmax 3435, 1007, 758 cm−1. Anal. Calcd for (C20H32O2): C, 78.90; H, 10.59. Found: C, 78.83; H, 10.77.

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 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3ee9a38a6232495dbc43cd6b13e01e4a
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

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