4-Toluenesulfonyl chloride → 2-(P-Tolylsulfonyl)-6-oxa-2-azaspiro[2.5]octane

HRID 1023827ノート

反応式

HRID 1023827 の反応式
[NH2:1][C:2]1([CH2:8]O)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>ClCCl.CN(C1C=CN=CC=1)C>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:1]2[C:2]3([CH2:7][CH2:6][O:5][CH2:4][CH2:3]3)[CH2:8]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

参加物

6

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 18316484(4-Aminooxan-4-yl)methanol

生成物 1

HCID 584326642-(P-Tolylsulfonyl)-6-oxa-2-azaspiro[2.5]octane収率 38.3%

試薬・触媒・溶媒 2

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

実験手順

A solution of 4-aminotetrahydro-2H-pyran-4-methanol (16 g, 122 mmol) in dichloromethane (700 mL) was treated with triethylamine (85 mL, 610 mmol), p-toluenesulfonyl chloride (69.8 g, 366 mmol) and DMAP (1490 mg, 12.2 mmol) under nitrogen. After approximately 18 hours at room temperature, the reaction was filtered through a pad of silica gel. The filtrate was concentrated in vacuo then purified by chromatography on silica gel (5-20% EtOAc/hexane) to afford intermediate the title compound (12.5 g) as a white solid.

後処理

  1. filtrationthe reaction was filtered through a pad of silica gel
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthen purified by chromatography on silica gel (5-20% EtOAc/hexane)

出典と根拠

ORDレコード
ord-ea84956d101c43f9b291da8d044e5740
出典データセット
uspto-grants-2014_05
特許番号
US08722727B2

反応ノート

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