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

HRID 422930Notes

Reaction equation

HRID 422930 reaction equation
[NH2:1][C@:2]([CH3:12])([CH2:5][CH2:6][C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)[CH2:3][OH:4].[C:13](OC(OC(C)(C)C)=O)(OC(C)(C)C)=[O:14].C(N(CC)CC)C.O>ClCCl.CN(C)C1C=CN=CC=1>[CH3:12][C@@:2]1([CH2:5][CH2:6][C:7]2[O:8][CH:9]=[CH:10][CH:11]=2)[CH2:3][O:4][C:13](=[O:14])[NH:1]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 66672879HCID 66672879, compound

Product 1

HCID 66672687(4R)-4-[2-(Furan-2-yl)ethyl]-4-methyl-1,3-oxazolidin-2-oneYield 58%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Subsequently, to a suspension of (2R)-2-amino-2-methyl-4-(furan-2-yl)butan-1-ol 1/2 D-(−)tartrate (51.2 mg, 0.16 mmol) obtained above 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 evaporated 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-(furan-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. 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-bbda76646f064e3e89584afa668e0fb2
Source dataset
uspto-grants-2012_01
Patent number
US08101650B2

Reaction notes

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