Water → (4R)-4-Methyl-4-[2-(1-methyl-1H-pyrrol-2-yl)ethyl]-1,3-oxazolidin-2-one

HRID 422935Notes

Reaction equation

HRID 422935 reaction equation
[NH2:1][C@:2]([CH3:13])([CH2:5][CH2:6][C:7]1[N:8]([CH3:12])[CH:9]=[CH:10][CH:11]=1)[CH2:3][OH:4].[C:14](OC(OC(C)(C)C)=O)(OC(C)(C)C)=[O:15].C(N(CC)CC)C.O>ClCCl.CN(C)C1C=CN=CC=1>[CH3:13][C@@:2]1([CH2:5][CH2:6][C:7]2[N:8]([CH3:12])[CH:9]=[CH:10][CH:11]=2)[CH2:3][O:4][C:14](=[O:15])[NH:1]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 66672978HCID 66672978, compound

Product 1

HCID 18448138(4R)-4-Methyl-4-[2-(1-methyl-1H-pyrrol-2-yl)ethyl]-1,3-oxazolidin-2-oneYield 53.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Subsequently, to a suspension of (2R)-2-amino-2-methyl-4-(1-methylpyrrol-2-yl)butan-1-ol 1/2 D-(−)tartrate (41.4 mg, 0.16 mmol) obtained above in dichloromethane (1.6 ml) was added successively di-t-butyl dicarbonate (0.1758 g, 0.81 mmol), triethylamine (0.225 ml, 1.62 mmol) and 4-dimethylaminopyridine (2.0 mg, 0.016 mmol) with stirring, and the resulting mixture was stirred at room temperature for 30 minutes. After stirring, water was added to the reaction mixture, and the resulting mixture was evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (3:2-2:1) as the eluent to afford (4R)-4-methyl-4-[2-(1-methylpyrrol-2-yl)ethyl]-1,3-oxazolidin-2-one (17.7 mg, yield: 53%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  2. stirringAfter stirring
  3. customthe resulting mixture was evaporated in vacuo
  4. customThe residue obtained
  5. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-0b7b9bfc2417435b855f208e6c32c974
Source dataset
uspto-grants-2012_01
Patent number
US08101650B2

Reaction notes

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