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

HRID 35873노트

반응식

HRID 35873 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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:

후처리

  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)

출처 및 근거

ORD 기록
ord-8941ec5c6e1d4a45a3c693a6e72a8d7f
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05411974

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