4-Toluenesulfonyl chloride → (R)-tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate

HRID 272713

反応式

HRID 272713 の反応式
[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C@@H:9]1[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O:11][CH2:10][C@H:9]2[CH2:12][CH2:13][CH2:14][N:8]2[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])(=[O:23])=[O:22])=[CH:17][CH:16]=1

参加物

6

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 688279N-(tert-Butoxycarbonyl)-D-prolinol

生成物 1

HCID 11760051(R)-tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate収率 45%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
40 °C

実験手順

A mixture of Boc-D-prolinol (201 mg, 1.0 mmol), p-toluenesulfonyl chloride (400 mg, 2.1 mmol), triethylamine (420 μL, 3.0 mmol), and 4-(dimethylamino)pyridine (12 mg, 0.1 mmol) in dichloromethane (10 mL) was heated at 40° C. for 48 hours, cooled to room temperature, concentrated under vacuum, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered, and concentrated. The residue was purified by column chromatography on silica gel to provide 160 mg (45%) of the desired product.

後処理

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under vacuum
  3. additiondiluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-d63fff0499e247fd9dceeb7f7da20f56
出典データセット
uspto-grants-2008_11
特許番号
US07456169B2

関連ノート

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