Water → (r)-5,5-Dimethyl-3-((tetrahydrofuran-2-yl)methyl)oxazolidin-2-imine

HRID 536733Notes

Reaction equation

HRID 536733 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][NH:7][C:8]#[N:9].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:16][C:17]1([CH3:20])[CH2:19][O:18]1.O>COCCOC>[CH3:16][C:17]1([CH3:20])[O:18][C:8](=[NH:9])[N:7]([CH2:6][C@H:2]2[CH2:3][CH2:4][CH2:5][O:1]2)[CH2:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 11208Isobutylene oxideHCID 55288151(R)-tetrahydrofuran-2-ylmethyl-cyanamide

Product 1

HCID 66643195(r)-5,5-Dimethyl-3-((tetrahydrofuran-2-yl)methyl)oxazolidin-2-imine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of Example 32A (0.6 g, 4.9 mmol), cesium carbonate (1.6 g, 4.9 mmol) and 2,2-dimethyloxirane (0.35 g, 4.9 mmol, Alfa-aesar) in 1,2-dimethoxyethane (20 mL) was heated to 80° C. overnight. The mixture was poured into water, and extracted with ethyl acetate (2×20 mL). The combined organic extracts were dried over Na2SO4, filtered, concentrated under reduced pressure to afford the title compound. LCMS (APCI+) m/z 198 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bf292abbcb3f4341ae4adb25ea40f9af
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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