Acetone → HCID 117970168, compound

HRID 2271315Notes

Reaction equation

HRID 2271315 reaction equation
[CH3:1][C:2]1[C:6](=[O:7])[O:5][C@@H:4]([O:8]/[CH:9]=[C:10]2\[C@H:11]3CC=C[C@H:12]3[NH:13][C:14]\2=[O:15])[CH:3]=1.C[N+]1([O-])CC[O:23]CC1.[CH3:27][C:28]([CH3:30])=[O:29].O>CC(O)(C)C.O=[Os](=O)(=O)=O>[OH:29][CH:28]1[CH:30]([OH:23])[C@H:12]2[NH:13][C:14](=[O:15])/[C:10](=[CH:9]/[O:8][C@H:4]3[CH:3]=[C:2]([CH3:1])[C:6](=[O:7])[O:5]3)/[C@H:11]2[CH2:27]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 82029Methyl morpholine oxideHCID 117970178HCID 117970178, compound

Product 1

HCID 117970168HCID 117970168, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolvent

Procedure

To a solution of (3E,3aR,6aR)-3-[[(2R)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylene]-1,3a,4,6a-tetrahydrocyclopenta[b]pyrrol-2-one Ia-1′ (137 mg, 0.55 mmol) in tBuOH (3 mL) was added NMO (77.9 mg, 0.67 mmol) and acetone (0.5 mL) followed by OsO4 (2.5-wt % in tBuOH, 560 mg, 0.055 mmol) and water (15 mg, 0.84 mmol). After 1 h at room temperature, H2Cl2 was added then the crude mixture was dried over Na2SO4, filtered and concentrated under reduced pressure. Purification using flash chromatography (CH2Cl2/MeOH, gradient) afforded the desired compound as a yellow foam (59 mg, 38%); 1H NMR (400 MHz, MeOH-d4) 7.25 (1H, d), 7.14 (1H, m), 6.34 (1H, m), 4.02 (1H, m), 3.84 (1H, dd), 3.76 (1H, dd), 3.55 (1H, m), 2.15 (1H, dt), 1.96 (3H, dd), 1.86 (1H, ddd): LCMS (Method D): 0.24 min; ES+282 (M+H+).

Workup

  1. additionH2Cl2 was added
  2. dry with materialthe crude mixture was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification

Sources & evidence

ORD record
ord-afeb402ec9d6463abf54f456cf9542aa
Source dataset
uspto-grants-2015_09
Patent number
US09119398B2

Reaction notes

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