Vinyl Acetate → HCID 11359478, compound

HRID 1870248Notes

Reaction equation

HRID 1870248 reaction equation
[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

Participants

4

Reactant 2

HCID 7904Vinyl AcetateHCID 11348115HCID 11348115, compound

Product 1

HCID 11359478HCID 11359478, compound

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-cb4580d3528a494384d8ce2b7086a9d8
Source dataset
uspto-grants-2000_08
Patent number
US06096736

Reaction notes

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