Toluene → (S)-4-(2-Hydroxy-2-methylpropyl)oxazolidin-2-one

HRID 1620925

反応式

HRID 1620925 の反応式
C[Mg]Br.[C:4]1([CH3:10])[CH:9]=C[CH:7]=[CH:6][CH:5]=1.C1C[O:14]CC1.[O:16]=[C:17]1[NH:21][C@@H](CC(OCC2C=CC=CC=2)=O)C[O:18]1>C(O)(=O)C.O>[OH:14][C:4]([CH3:10])([CH3:9])[CH2:5][C@H:6]1[CH2:7][O:18][C:17](=[O:16])[NH:21]1

参加物

7

反応物 4

HCID 1140TolueneHCID 8028Tetrahydrofuran2 回HCID 11241814(S)-Benzyl 2-(2-oxooxazolidin-4-YL)acetateHCID 178418573HCID 178418573、化合物

生成物 1

HCID 11321109(S)-4-(2-Hydroxy-2-methylpropyl)oxazolidin-2-one

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

Methylmagnesium bromide (227 mL of 3M solution in diethyl ether) was added to a mixture of toluene (340 mL) and THF (340 mL) at −20° C. A warm THF solution (170 mL) of the ester from Step 2 (40 g) was then added dropwise maintaining the temperature below −10° C. The mixture was aged for 2 hours and was then slowly added to a mixture of water (1000 mL) and acetic acid (200 mL) and the resultant mixture was stirred for 2 hours at room temperature. The aqueous layer was separated and the organic layer was extracted with water (2×200 mL). The product was extracted from the combined aqueous layers using dichloromethane and a continuous extractor. The dichloromethane extract was evaporated to dryness using heptane as a co-solvent to azeotrope off the acetic acid. The residue was purified by chromatography on SiO2 using ethanol and dichloromethane (1:30) to yield (4S)-4-(2-hydroxy-2-methylpropyl)-1,3-oxazolidin-2-one.

後処理

  1. temperaturemaintaining the temperature below −10° C
  2. customThe aqueous layer was separated
  3. extractionthe organic layer was extracted with water (2×200 mL)
  4. extractionThe product was extracted from the combined aqueous layers
  5. extractionThe dichloromethane extract
  6. customwas evaporated to dryness
  7. customThe residue was purified by chromatography on SiO2

出典と根拠

ORDレコード
ord-7754505be25e48b09c7d441897047589
出典データセット
uspto-grants-2014_07
特許番号
US08772336B2

関連ノート

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