Methanesulfonyl chloride → Benzyl 4-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate

HRID 1291851

反応式

HRID 1291851 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][OH:23])[CH2:18][CH2:17]1)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>ClCCl>[CH2:6]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][O:23][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:18][CH2:17]1)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

4

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 736490Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate

生成物 1

HCID 28820646Benzyl 4-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
5 °C

実験手順

A solution of methanesulphonylchloride (7.7 ml) in dichloromethane (50 ml) was added dropwise to a stirred solution of 1-benzyloxycarbonyl-4-hydroxymethylpiperidine (23.4 g) in dichloromethane (350 ml) cooled to 5° C. Stirring was continued for 1 hour, then the solution was washed with water (4×150 ml) and saturated aqueous sodium chloride (100 ml), dried and concentrated. The residue was crystallised from tetrachloromethane (250 ml) to give 1-benzyloxycarbonyl-4-methanesulphonyloxymethylpiperidine (20 g) as colourless prisms, m.p. 72°-74° C. NMR (CDCl3): δ 1.1-1.4(2H,m); 1.7-1.8(2H,d); 1.9-2.1(1H,m); 2.7-2.9(2H,t); 3.0(3H,s); 4.05(2H,d); 4.1-4.4(2H,d); 5.1(2H,s); 7.3(5H,m); m/e 328(M+H)+ 350 (M+Na)+ ; calculated for C15H21N5O5 : C, 55.0; H, 6.5; N, 4.3; found: C, 54.8; H, 6.6; N, 4.2%.

後処理

  1. washthe solution was washed with water (4×150 ml) and saturated aqueous sodium chloride (100 ml)
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was crystallised from tetrachloromethane (250 ml)

出典と根拠

ORDレコード
ord-e8809c47fe7e456db26688b89324cd47
出典データセット
uspto-grants-1998_05
特許番号
US05753659

関連ノート

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