Water → HCID 90388631, compound

HRID 2201743Notes

Reaction equation

HRID 2201743 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])[CH2:16][C:17](=[O:19])[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([CH2:17][O:19]3)[CH2:22][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 90387884HCID 90387884, compound

Product 1

HCID 90388631HCID 90388631, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of compound 45 (45 mg, 0.16 mmol) in DMSO (3 mL) was added trimethylsulfonium iodide (202 mg, 1.0 mmol) and potassium tert-butoxide (112 mg, 1.0 mmol) at room temperature. After 3 h, water was added (20 mL) 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 46 (35 mg, 75%) as a white solid: mp 165-167° C.; [α]D25 +20.0 (c 0.12, CHCl3); 1H NMR (CDCl3) δ 4.08 (s, 1H), 2.90 (d, J=15.2 Hz, 1H), 2.60 (d, J=15.2 Hz, 1H), 0.87 (s, 3H); 13C NMR (CDCl3) δ 70.5, 66.5, 53.6, 48.3, 47.2, 47.0, 42.1, 40.4, 40.2, 37.9, 36.2, 34.2, 34.0, 32.8, 29.0, 28.8, 25.8, 23.3, 14.3; IR νmax 3418, 1443, 1378, 851 cm−1. MS (FAB) for [C19H30O2]+: 290.2246. Found: 290.2243.

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-0608f4d3cdbd4d0282d722c4e05a5ce7
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

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