Sodium Thiosulfate → 1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl]-2,2,2-trifluoroethan-1-one

HRID 35870ノート

反応式

HRID 35870 の反応式
[CH2:1]([N:8]([CH3:26])[C:9]([CH2:11][CH2:12][C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]([OH:25])[C:21]([F:24])([F:23])[F:22])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CCOCC.C(Cl)Cl>[CH2:1]([N:8]([CH3:26])[C:9]([CH2:11][CH2:12][C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 14995339(1RS)-1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-yl]-2,2,2-trifluoroethanol

生成物 1

HCID 156609871-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl]-2,2,2-trifluoroethan-1-one収率 50.8%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of (1RS)-1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-yl]-2,2,2-trifluoroethanol (103 mg), Dess-Martin reagent (435 mg) and methylene chloride (1.5 ml) was stirred for 3 hrs. at room temperature. After reaction, the raction solution was diluted with ether. The diluted solution was added dropwise to a saturated aq. solution of sodium bicarbonate (30) wherein sodium thiosulfate (3.0 g) was dissolved. The mixture was stirred for 10 mins at room temperature. The mixture was extracted with EtOAc. The extract was washed, dried and evaporated. The residue was purified by column chromatography on silica gel (hexane - EtOAc) to give the title compound (52 mg) having the following physical data:

後処理

  1. customat room temperature
  2. customAfter reaction
  3. dissolutionwas dissolved
  4. stirringThe mixture was stirred for 10 mins at room temperature
  5. extractionThe mixture was extracted with EtOAc
  6. washThe extract was washed
  7. customdried
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel (hexane - EtOAc)

出典と根拠

ORDレコード
ord-eb993f1e9ab7437caa0bab53a853a7d2
出典データセット
uspto-grants-1995_05
特許番号
US05411974

反応ノート

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