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

HRID 422939Notes

Reaction equation

HRID 422939 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>ClCCl.CN(C)C1C=CN=CC=1>[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

7

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 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Subsequently, to a suspension of (2R)-2-amino-2-methyl-4-(1-ethylpyrrol-2-yl)butan-1-ol 1/2 D-(−)tartrate (55.5 mg, 0.16 mmol) in dichloromethane (1.6 ml) were added successively 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) with stirring, and the resulting mixture was stirred at room temperature for 20 minutes. After stirring, water was added to the reaction mixture, and the resulting mixture was concentrated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (1:1) as the eluent to afford (4R)-4-methyl-4-[2-(1-ethylpyrrol-2-yl)ethyl]-1,3-oxazolidin-2-one (18.0 mg, yield: 58%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 20 minutes
  2. stirringAfter stirring
  3. concentrationthe resulting mixture was concentrated in vacuo
  4. customThe residue obtained
  5. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-20656771faf549e1a83c5e1f4a603ec2
Source dataset
uspto-grants-2012_01
Patent number
US08101650B2

Reaction notes

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