Water → (R)-4-(2-(1-Ethyl-1H-pyrrol-2-yl)ethyl)-4-methyloxazolidin-2-one

HRID 604563Notes

Reaction equation

HRID 604563 reaction equation
[NH2:1][C@:2]([CH3:14])([CH2:5][CH2:6][C:7]1[N:8]([CH2:12][CH3:13])[CH:9]=[CH:10][CH:11]=1)[CH2:3][OH:4].[C:15](OC(OC(C)(C)C)=O)(OC(C)(C)C)=[O:16].C(N(CC)CC)C.O>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH3:14][C@@:2]1([CH2:5][CH2:6][C:7]2[N:8]([CH2:12][CH3:13])[CH:9]=[CH:10][CH:11]=2)[CH2:3][O:4][C:15](=[O:16])[NH:1]1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 18448118(2R)-2-amino-2-methyl-4-(1-ethylpyrrol-2-yl)butan-1-ol

Product 1

HCID 45095485(R)-4-(2-(1-Ethyl-1H-pyrrol-2-yl)ethyl)-4-methyloxazolidin-2-oneYield 58%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The thus obtained (2R)-2-amino-2-methyl-4-(1-ethylpyrrol-2-yl)butan-1-ol ½ D-(−)-tartrate (55.5 mg, 0.160 mmol) was suspended in methylene chloride (1.6 mL) and di-t-butyl dicarbonate (0.17 g, 0.78 mmol), triethylamine (0.22 mL, 1.58 mmol) and 4-dimethylaminopyridine (3.0 mg, 0.025 mmol) were added thereto, followed by stirring of the mixture at room temperature for 20 minutes. Water and ethyl acetate were added thereto to separate it. The thus obtained organic phase was separated and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethyl acetate, 1:1) to obtain (4R)-4-methyl-4-[2-(1-ethylpyrrol-2-yl)ethyl]-1,3-oxazolidin-2-one (18.0 mg, yield: 58%).

Workup

  1. customto separate it
  2. customThe thus obtained organic phase was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-627443735c97443697898c2ee72e7ff2
Source dataset
uspto-grants-2011_03
Patent number
US07910617B2

Reaction notes

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