Trimethylsulfonium iodide → HCID 90388258, compound

HRID 2201750Notes

Reaction equation

HRID 2201750 reaction equation
[OH:1][CH: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>[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

5

Reactant 3

HCID 75127Trimethylsulfonium iodideHCID 23665647Potassium tert-butoxideHCID 90388597HCID 90388597, compound

Product 1

HCID 90388258HCID 90388258, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of compound 55 (40 mg, 0.144 mmol) in DSMO (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 56 (27 mg, 65%) as a white solid: mp 163-165° C.; [α]D25 +16.7 (c 0.12, CHCl3); 1H NMR (CDCl3) δ 3.64-3.60 (m, 1H), 2.90 (d, J=15.0 Hz, 1H), 2.61 (d, J=15.2 Hz, 1H), 0.86 (s, 3H); 13C NMR (CDCl3) δ 71.7, 70.5, 53.6, 47.1, 41.6, 40.7, 39.1, 38.6, 38.1, 36.2, 35.1, 35.0, 33.6, 33.0, 30.4, 29.8, 28.9, 25.6, 14.5; IR νmax 3379, 1443, 1375 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-66fedbe1f021442899a689ec3a1e9456
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

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