Imidazole → (R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)oxazolidin-2-one

HRID 57358Notes

Reaction equation

HRID 57358 reaction equation
N1C=CN=C1.[OH:6][CH2:7][C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1.[C:14]([Si:18](Cl)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl.O>[Si:18]([O:6][CH2:7][C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 14456890(4S)-4-(hydroxymethyl)-1,3-oxazolidin-2-one

Product 1

HCID 89766177(R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)oxazolidin-2-oneYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Imidazole (1.74 g, 25.6 mmol, 2.0 equiv) was added to a solution of (S)-4-(hydroxymethyl)oxazolidin-2-one (1.5 g, 12.8 mmol) and tert-butylchlorodiphenylsilane (3.95 mL, 15.4 mmol, 1.2 equiv) in DCM (43 mL) at room temperature. A white precipitate formed. The solution was stirred at room temperature for 16 hours and then diluted with water (50 mL). The layers were separated and the aqueous layer was extracted with DCM (50 mL). The combined organic extracts were washed with saturated aqueous sodium chloride (50 mL), dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (EtOAc/Heptane 20 to 65%) provided (R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)oxazolidin-2-one (3.55 g, sticky colorless oil) in 78% yield. 1H NMR (400 MHz, CDCl3) δ 7.64 (m, 4H), 7.50-7.38 (m, 6H), 5.31 (m, 1H), 4.44 (t, J=8.7 Hz, 1H), 4.15 (m, 1H), 4.00 (m, 1H), 3.65 (d, J=5.5 Hz, 2H), 1.07 (s, 9H). MS m/z 356.1 (M+H)+; Rt-1.00 min.

Workup

  1. customA white precipitate formed
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with DCM (50 mL)
  4. washThe combined organic extracts were washed with saturated aqueous sodium chloride (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1785044e25b743c8b515b7b55bf8bbbe
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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