3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (S)-(-)- → HCID 10946477、化合物

HRID 238572

反応式

HRID 238572 の反応式
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH:13]=[O:14])[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:17][C:18]([Si](C)(C)C)([F:20])[F:19].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:15][C:9]1([CH3:16])[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:12]([CH:13]([OH:14])[C:18]([F:20])([F:19])[F:17])[CH2:11][O:10]1

参加物

6

反応物 3

HCID 1798243-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (S)-(-)-HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride

生成物 1

HCID 10946477HCID 10946477、化合物収率 92.7%

試薬・触媒・溶媒 2

HCID 2724141Tetrabutylammonium Fluoride触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of (S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.0 g, 4.36 mmol), (trifluoromethyl)trimethylsilane (2.0 M solution in THF, 2.6 mL, 5.20 mmol) in THF (10 mL) was added tetrabutylammonium fluoride (1.0 M solution in THF, 0.1 mL, 0.10 mmol) at 0° C. After addition, the mixture was stirred at room temperature for 60 h. Then, tetrabutylammonium fluoride (1.0 M solution in THF, 9 mL, 9.0 mmol) was added and the mixture stirred for another 6 h and subsequently quenched by adding saturated aq. NaHCO3 solution, extracted with EtOAc. The extracts were washed with saturated aq. NaHCO3 solution, water, brine and dried over Na2SO4. Concentration and purification gave (S)-tert-butyl 2,2-dimethyl-4-(2,2,2-trifluoro-1-hydroxyethyl)oxazolidine-3-carboxylate (1.21 g, 92%), which showed a complicated NMR spectrum because of the different comformers.

後処理

  1. additionAfter addition
  2. stirringthe mixture stirred for another 6 h
  3. customsubsequently quenched
  4. additionby adding saturated aq. NaHCO3 solution
  5. extractionextracted with EtOAc
  6. washThe extracts were washed with saturated aq. NaHCO3 solution, water, brine
  7. dry with materialdried over Na2SO4
  8. concentrationConcentration and purification

出典と根拠

ORDレコード
ord-93324d6f5b2344c5b14a673db5d4e78e
出典データセット
uspto-grants-2014_02
特許番号
US08642632B2

関連ノート

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