Cyclopentanone → HCID 59090746, 화합물

HRID 29185노트

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HRID 29185 반응식
[CH2:1]([C@H:8]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:9]([OH:13])[CH2:10][NH:11][NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1(=O)[CH2:26][CH2:25][CH2:24][CH2:23]1>C(O)(C)C>[CH2:1]([C@H:8]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[C@H:9]([OH:13])[CH2:10][NH:11][N:12]=[C:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 8452CyclopentanoneHCID 59090665tert-butyl N-[(1S,2R)-1-benzyl-3-hydrazino-2-hydroxypropyl]carbamate

생성물 1

HCID 59090746HCID 59090746, 화합물수율 14%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A solution of tert-butyl N-[(1S,2R)-1-benzyl-3-hydrazino-2-hydroxypropyl]carbamate (500 mg, 1.695 mmol) in 5 mL of isopropanol under Argon was treated with cyclopentanone (180 μL, 2.034 mmol). After stirring for approximately 18 hours, the reaction solvent was removed in vacuo and the residue was triturated with diethylether. The slurry was filtered and the solid was dried under high vacuum to provide tert-butyl N-[(1S,2R)-1-benzyl-3-(2-cyclopentylidenhydrazino)-2-hydroxypropyl]carbamate (85 mg, 14%) as a white solid. H1-NMR (chloroform-D3) 1.34 (s, 9H), 1.54 (b, 2H), 1.73 (m, 2H), 1.83 (m, 2H), 2.22 (m, 2H), 2.35 (m, 2H), 2.90 (m, 1H), 3.02 (m, 1H), 3.14 (m, 1H), 3.38 (m, 1H), 3.64 (bm, 1H), 3.84 (bm, 1H), 4.52 (m, 1H), 7.25 (m, 5H). MS(APCI): 361(M+Na).

후처리

  1. customthe reaction solvent was removed in vacuo
  2. customthe residue was triturated with diethylether
  3. filtrationThe slurry was filtered
  4. customthe solid was dried under high vacuum

출처 및 근거

ORD 기록
ord-dc0c7637ad52455c8faa1f088ac154a1
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419967B2

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