Vinyl Acetate → HCID 11359478, 화합물

HRID 1870248노트

반응식

HRID 1870248 반응식
[OH:1][CH2:2][CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:6][CH2:5][CH2:4]1.C(OC=C)(=O)C>C(OC(C)C)(C)C>[OH:1][CH2:2][C@@H:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([S:14]([C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH2:6][CH2:5][CH2:4]1

참가 물질

4

반응물 2

HCID 7904Vinyl AcetateHCID 11348115HCID 11348115, 화합물

생성물 1

HCID 11359478HCID 11359478, 화합물

시약·촉매·용매 1

HCID 7914Diisopropyl Ether용매

실험 절차

5-Hydroxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (9.94 g) is dissolved in diisopropyl ether (150 ml), and thereto are added with stirring vinyl acetate (7.75 g) and Lipase QL (8%) (0.80 g) at -2° C. The mixture is stirred at -2° C. to 1° C. for 1.5 hour. The Lipase QL is removed by filtration on celite, and the filtrate is evaporated under reduced pressure, and the resulting residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=3:1→1:1) to give (5S)-5-hydroxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (hereinafter, referred to as Compound C) (4.54 g) and (5R)-5-acetyloxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (hereinafter, referred to as Compound D) (5.63 g).

후처리

  1. customThe Lipase QL is removed by filtration on celite
  2. customthe filtrate is evaporated under reduced pressure
  3. customthe resulting residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=3:1→1:1)

출처 및 근거

ORD 기록
ord-cb4580d3528a494384d8ce2b7086a9d8
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06096736

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