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

HRID 1269409Notes

Reaction equation

HRID 1269409 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 ½ 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-f76210bd3f2d468c9beaf167334ca3ae
Source dataset
uspto-grants-2007_04
Patent number
US07199150B2

Reaction notes

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