Methanesulfonyl chloride → 1-Methanesulfonyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine

HRID 237487ノート

反応式

HRID 237487 の反応式
[Cl-].[CH3:2][C:3]1([CH3:16])[C:7]([CH3:9])([CH3:8])[O:6][B:5]([C:10]2[CH2:11][CH2:12][NH2+:13][CH2:14][CH:15]=2)[O:4]1.C(N(C(C)C)C(C)C)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH3:26][S:27]([N:13]1[CH2:12][CH:11]=[C:10]([B:5]2[O:4][C:3]([CH3:16])([CH3:2])[C:7]([CH3:8])([CH3:9])[O:6]2)[CH2:15][CH2:14]1)(=[O:29])=[O:28]

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 898085294-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridin-1-ium chloride

生成物 1

HCID 679734971-Methanesulfonyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a cooled (0° C.) solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridinium chloride (8 g) and N-ethyldiisopropylamine (12 mL) in dichloromethane (100 mL) is added dropwise methanesulfonyl chloride (3 mL). The mixture is stirred for 12 hours at room temperature. The mixture is partitioned between dichloromethane and 0.1 M hydrochloric acid. The organic phase is separated, washed with brine and dried (MgSO4). The solvent is evaporated and the residue is crystallized from diethylether to give the title compound. Yield: 7.4 g; LC (method 15): tR=0.98 min; Mass spectrum (ESI+): m/z=288 [M+H]+.

後処理

  1. customThe mixture is partitioned between dichloromethane and 0.1 M hydrochloric acid
  2. customThe organic phase is separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent is evaporated
  6. customthe residue is crystallized from diethylether

出典と根拠

ORDレコード
ord-3a7a1c1e56a247f7b95f16056621c0d7
出典データセット
uspto-grants-2014_02
特許番号
US08642585B2

反応ノート

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