Dimethyl Sulfoxide → HCID 57786532, compound

HRID 253583Notes

Reaction equation

HRID 253583 reaction equation
[H-].[Na+].[CH3:3]S(C)=O.[O:7]=[CH:8][C@@H:9]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:10][CH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>C1COCC1.[Cl-].[Na+].O>[O:7]1[CH2:3][CH:8]1[C@@H:9]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:23])[CH3:22])[CH2:10][CH:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydride2×HCID 57786539HCID 57786539, compound

Product 1

HCID 57786532HCID 57786532, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A 100 mL flask was charged with NaH (116 mg, 2.9 mmol) and Me3S+OI− (639 mg, 2.9 mmol) under N2. Dry DMSO (6 mL) was added. The mixture was stirred at rt for 1 h. A second 100 mL flask was charged with (S)-tert-butyl 1-oxo-3-(tetrahydro-2H-pyran-4-yl)propan-2-ylcarbamate (500 mg, 1.9 mmol) dissolved in THF (5 mL) under N2. The solution of NaH and Me3S+OI− was added through a syringe. The resulting mixture was stirred for 1 h. at rt. Brine was added and the mixture was extracted with EtOAc (3×10 mL). The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography to give tert-butyl (1S)-1-(oxiran-2-yl)-2-(tetrahydro-2H-pyran-4-yl)ethylcarbamate (150 mg, 29%). 1H NMR (CD3OD) δ 1.45 (s, 9H), 2.60 (b, 1 h), 2.75 (m, 1H), 3.0 (b, 1H), 3.35 (m, 2H), 4.0 (m, 3H), 4.30 (b, 1H), 5.30 (s, 2H).

Workup

  1. stirringThe resulting mixture was stirred for 1 h. at rt
  2. extractionthe mixture was extracted with EtOAc (3×10 mL)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-462ff61288424279aa1c3c301da6baf2
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

Loading…