Cyclopentanone → HCID 59090746、化合物

HRID 29185ノート

反応式

HRID 29185 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 59090746HCID 59090746、化合物収率 14%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-dc0c7637ad52455c8faa1f088ac154a1
出典データセット
uspto-grants-2008_09
特許番号
US07419967B2

反応ノート

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