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Hydrochloric Acid → 2-Ethoxy-3-(2,2,2-trifluoro-acetylamino)-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1976548
ノート
印刷プレビュー

反応式

HRID 1976548 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[C:12]1=[O:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[CH2:37](O)[CH3:38]>O1CCOCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([NH:16][C:17](=[O:22])[C:18]([F:21])([F:19])[F:20])[CH:12]1[O:23][CH2:37][CH3:38])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 6

HCID 313Hydrochloric Acid2 回HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride2 回HCID 107114652-Oxo-3-(2,2,2-trifluoro-acetylamino)-pyrrolidine-1-carboxylic acid benzyl ester

生成物 1

HCID 54116192
2-Ethoxy-3-(2,2,2-trifluoro-acetylamino)-pyrrolidine-1-carboxylic acid benzyl ester

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

To Intermediate 4 (34 g) in ethanol (1070 ml) at −5° C. was added sodium borohydride (9.86 g). A solution of 4M hydrogen chloride in 1,4-dioxan (20 ml) was then added dropwise. Periodically further portions of 4M hydrogen chloride in 1,4-dioxan (2×5 ml, 1×10 ml) and sodium borohydride (2 g) were added. After 3 h, concentrated sulphuric acid (11 ml) was added and the mixture warmed to room temperature for 2 h. Saturated aqueous sodium bicarbonate (300 ml) was then added and the ethanol and dioxan removed in vacuo. The residue was diluted with water (500 ml) and extracted with ethyl acetate (3×500 ml). The combined extracts were washed with brine and dried (MgSO4). The solvent was removed in vacuo and the residue purified by flash chromatography on silica gel 9385 eluting with ether, to give the title compound (21 g). Mass spec. MNH4+ (found) 378 MNH4+ (calculated) 378

後処理

  1. customthe ethanol and dioxan removed in vacuo
  2. additionThe residue was diluted with water (500 ml)
  3. extractionextracted with ethyl acetate (3×500 ml)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customthe residue purified by flash chromatography on silica gel 9385 eluting with ether

出典と根拠

ORDレコード
ord-e6574531a0d24c5a8f58e16e3fbf49e0
出典データセット
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06228853B1

反応ノート

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