D-Proline → HCID 57786523、化合物

HRID 253579

反応式

HRID 253579 の反応式
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][CH:9]=[O:10])[CH2:3][CH2:2]1.[N:11]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])=[N:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].C1CN[C@@H](C(O)=O)C1.[BH4-].[Na+]>CC#N.C(O)C>[OH:10][CH2:9][C@@H:8]([N:11]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1

参加物

7

反応物 4

HCID 8988D-ProlineHCID 755571,2-Bis(phenylmethyl) 1,2-diazenedicarboxylateHCID 4311764Sodium borohydrideHCID 574496833-(TETRAHYDRO-2H-PYRAN-4-YL)PROPANAL

生成物 1

HCID 57786523HCID 57786523、化合物収率 89%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 3-(tetrahydro-pyran-4-yl)-propionaldehyde (8.59 g, 0.06 mol) and dibenzyl azodicarboxylate (12.8 g, 0.042 mol) in MeCN (250 mL) at 0° C. was added (R-proline) (0.48 g, 0.0042 mol). After stirring the mixture at 0° C. for 15 h, ethanol (100 mL) and NaBH4 (1.56 g, 0.042 mol) were added, and the mixture was stirred at 0° C. for 40 min. The reaction was quenched by slow addition of 10% aq citric acid (15 mL), and the whole solution was concentrated in vacuo. This residue was diluted with EtOAc (200 mL), washed with brine (50 mL), dried over Na2SO4, and concentrated in vacuo to give crude product which was purified by column chromatography to give (S)-dibenzyl 1-(1-hydroxy-3-(tetrahydro-2H-pyran-4-yl)propan-2-yl)hydrazine-1,2-dicarboxylate (16.52 g, 89%). 1H NMR (CD3OD) δ 1.0-1.5 (m, 8H), 2.9-3.3 (m, 2H), 3.4-3.6 (m, 2H), 3.7-3.9 (m, 2H), 4.4-4.7 (m, 2H), 5.1-5.4 (m, 4H), 7.2-7.4 (m, 10H).

後処理

  1. stirringthe mixture was stirred at 0° C. for 40 min
  2. customThe reaction was quenched by slow addition of 10% aq citric acid (15 mL)
  3. concentrationthe whole solution was concentrated in vacuo
  4. additionThis residue was diluted with EtOAc (200 mL)
  5. washwashed with brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto give crude product which
  9. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-e081292ec63447d6af8e1dcf1288bce3
出典データセット
uspto-grants-2011_01
特許番号
US07872028B2

関連ノート

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