Trifluoroacetic acid → (S)-3-((3R,4S)-1-benzyl-4-phenyl-pyrrolidine-3-carbonyl)-4-phenyl-oxazolidin-2-one

HRID 657712

反応式

HRID 657712 の反応式
[CH2:1]([N:8]([CH2:12][Si](C)(C)C)[CH2:9]OC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]1([C@H:23]2[CH2:27][O:26][C:25](=[O:28])[N:24]2[C:29](=[O:38])/[CH:30]=[CH:31]/[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.ClCCl>[CH2:1]([N:8]1[CH2:12][C@H:31]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C@@H:30]([C:29]([N:24]2[C@@H:23]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:27][O:26][C:25]2=[O:28])=[O:38])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 516892Sodium BicarbonateHCID 679769(4S)-4-Phenyl-3-(3-phenylprop-2-enoyl)-1,3-oxazolidin-2-one

生成物 1

HCID 54539415(S)-3-((3R,4S)-1-benzyl-4-phenyl-pyrrolidine-3-carbonyl)-4-phenyl-oxazolidin-2-one収率 64.7%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

N-Benzyl-N-(methoxymethyl)trimethylsilylmethylamine (10.03 g, 40.5 mmol) was added to (S)-4-phenyl-3-[(E)-(3-phenyl-acryloyl)]-oxazolidin-2-one (10.3 g, 35.1 mmol) in toluene (150 mL) at 0° C. and stirred for 20 minutes. Trifluoroacetic acid (9.7 mL) in dichloromethane (125 mL) was added dropwise to the reaction mixture keeping the internal temperature at 0° C. The reaction was stirred at room temperature overnight. The reaction mixture was poured into saturated sodium bicarbonate (200 mL) and extracted with dichloromethane (2×75 mL). The combined organic phases were washed with brine and dried over sodium sulfate. The organic phases were concentrated to give a waxy solid, which was purified by flash silica gel chromatography eluting with ethyl acetate:hexanes (1:9) to give 9.68 g (61%) of (S)-3-((3R,4S)-1-benzyl-4-phenyl-pyrrolidine-3-carbonyl)-4-phenyl-oxazolidin-2-one.

後処理

  1. customat 0° C
  2. stirringThe reaction was stirred at room temperature overnight
  3. extractionextracted with dichloromethane (2×75 mL)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationThe organic phases were concentrated
  7. customto give a waxy solid, which
  8. customwas purified by flash silica gel chromatography
  9. washeluting with ethyl acetate:hexanes (1:9)

出典と根拠

ORDレコード
ord-7db2a4b899d547ae9bf15a5580b6d335
出典データセット
uspto-grants-2011_12
特許番号
US08076349B2

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