Potassium Carbonate → 3-Hydroxybutyl 4-methylbenzenesulfonate

HRID 55657

반응식

HRID 55657 반응식
[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-:4])(=[O:3])=[O:2].F[C:13]1C=C[C:16]2C(C3CCNCC3)=N[O:19][C:15]=2[CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O:4][CH2:13][CH2:14][CH:15]([OH:19])[CH3:16])(=[O:3])=[O:2]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 85570p-ToluenesulfonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

생성물 1

HCID 132043233-Hydroxybutyl 4-methylbenzenesulfonate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Racemic 3-hydroxybutyl tosylate was prepared in a manner described by Ferreira et al., Tetrahedron, 46, pp. 6311-6318, (1990). To a solution of the racemic tosylate (9.2 g, 37.7 mmol) in acetonitrile (190 ml) was added 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (8.3 g, 37.7 mmol) followed by milled potassium carbonate (7.8 g, 56.6 mmol) at room temperature under nitrogen. The reaction mixture was warmed to reflux for 4.5 hours and allowed to cool to room temperature. The solids were removed via filtration through a pad of Celite and were washed with EtOAc. The combined filtrates were concentrated to give the crude product. Purification via preparative HPLC (silica gel, 10% MeOH/EtOAc) afforded 6.3 g (57%), m.p.=100°-102° C.

후처리

  1. temperatureThe reaction mixture was warmed
  2. temperatureto reflux for 4.5 hours
  3. customThe solids were removed via filtration through a pad of Celite
  4. washwere washed with EtOAc
  5. concentrationThe combined filtrates were concentrated

출처 및 근거

ORD 기록
ord-797004f80d3845da8a7dc9337628d0d5
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624927

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