Ammonium Chloride → (1RS)-1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl]-propan-1-ol

HRID 35873ノート

反応式

HRID 35873 の反応式
[CH2:1]([N:8]([CH3:22])[C:9]([CH2:11][CH2:12][C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]=[O:21])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([Mg]Cl)[CH3:24].[Cl-].[NH4+]>C1COCC1>[CH2:1]([N:8]([CH3:22])[C:9]([CH2:11][CH2:12][C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]([OH:21])[CH2:23][CH3:24])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 14674666(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-alHCID 178461633HCID 178461633、化合物

生成物 1

HCID 15660996(1RS)-1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl]-propan-1-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of (2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-al (700 mg) in THF (5 ml) was cooled to -25° C. A solution of ethyl magnesium chloride in THF (2M, 1.5 ml) was added dropwise to the solution. The mixture was stirred for 30 mins at the same temperature, and for 30 mins at 0° C. and further 1 hr. at room temperature. After reaction, a saturated aq. solution of ammonium chloride was added to the mixture. The oily layer separated was washed, dried and evaporated. The residue was purified by column chromatography on silica gel (EtOAc - CH3OH) to give the title compound (270 mg) having the following physical data:

後処理

  1. waitfor 30 mins at 0° C.
  2. customfurther 1 hr
  3. customat room temperature
  4. customAfter reaction
  5. customThe oily layer separated
  6. washwas washed
  7. customdried
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel (EtOAc - CH3OH)

出典と根拠

ORDレコード
ord-8941ec5c6e1d4a45a3c693a6e72a8d7f
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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