Trifluoromethanesulfonic acid → (S)-7-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)]-1,2,6,7,8,12b-hexahydro-6-oxopyrido[2,1-a][2]benzazepine

HRID 342897

Reaction equation

HRID 342897 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C@@H:12]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:13]([N:15]1[CH:20]=[CH:19][CH2:18][CH:17]=[CH:16]1)=[O:14].FC(F)(F)S(O)(=O)=O.C(OCC)(=O)C.CCCCCC>ClCCl>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[C@H:12]1[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH:16]2[CH2:17][CH2:18][CH:19]=[CH:20][N:15]2[C:13]1=[O:14]

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acid2×HCID 15380836(S)-N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,4-dihydro-pyridineHCID 21226206Ethyl acetate hexane2×

Product 1

HCID 9863597(S)-7-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)]-1,2,6,7,8,12b-hexahydro-6-oxopyrido[2,1-a][2]benzazepine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add a solution of (S)-N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,4-dihydro-pyridine (1.1 g, 3.1 mmol) in dichloromethane (2 mL) to trifluoromethanesulfonic acid (1.2 mL). After 2.5 hours, add trifluoromethanesulfonic acid (1.2 mL). After 4 hours, partition the reaction mixture between ethyl acetate and 5% sodium bicarbonate solution. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 10% ethyl acetate/hexane and then 25% ethyl acetate/hexane to give the title compound.

Workup

  1. waitAfter 4 hours
  2. custompartition the reaction mixture between ethyl acetate and 5% sodium bicarbonate solution
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customto give a residue

Sources & evidence

ORD record
ord-2eb4d8552f4f4a408ade09b297389eb8
Source dataset
uspto-grants-1999_01
Patent number
US05859252

Linked notes

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