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

HRID 237487노트

반응식

HRID 237487 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-3a7a1c1e56a247f7b95f16056621c0d7
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642585B2

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