4-Methylmorpholine → 1,8-diacetyl-5-{[(4-nitrophenoxy)carbonyl]oxy}-2,3,8,8a-tetrahydropyrrolo[2,3-b]indol-3a(1H)-yl acetate

HRID 78694Notes

Reaction equation

HRID 78694 reaction equation
[C:1]([O:4][C:5]12[CH2:20][CH2:19][N:18]([C:21](=[O:23])[CH3:22])[CH:6]1[N:7]([C:15](=[O:17])[CH3:16])[C:8]1[C:13]2=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)(=[O:3])[CH3:2].CN1CCOCC1.Cl[C:32]([O:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1)=[O:33]>O1CCCC1>[C:1]([O:4][C:5]12[CH2:20][CH2:19][N:18]([C:21](=[O:23])[CH3:22])[CH:6]1[N:7]([C:15](=[O:17])[CH3:16])[C:8]1[C:13]2=[CH:12][C:11]([O:14][C:32]([O:34][C:35]2[CH:36]=[CH:37][C:38]([N+:41]([O-:43])=[O:42])=[CH:39][CH:40]=2)=[O:33])=[CH:10][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 821294-Nitrophenyl chloroformateHCID 780110921,8-diacetyl-5-hydroxy-2,3,8,8a-tetrahydropyrrolo[2,3-b]indol-3a(1H)-yl acetate

Product 1

HCID 779859911,8-diacetyl-5-{[(4-nitrophenoxy)carbonyl]oxy}-2,3,8,8a-tetrahydropyrrolo[2,3-b]indol-3a(1H)-yl acetateYield 11.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the solution of 1,8-diacetyl-5-hydroxy-2,3,8,8a-tetrahydropyrrolo[2,3-b]indol-3a(1H)-yl acetate (88 mg; 0.28 mmol) in N-methylmorpholine (62 μl, 0.56 mmol) and small amount of tetrahydrofuran, the 4-nitrophenyl chloroformate (112.9 mg; 0.56 mmol) dissolved in tetrahydrofuran was added. Reaction was carried out for 3 days under an argon atmosphere. The solvent was evaporated. The residue was purified by column chromatography (SiO2, cyclohexane/methylene chloride/methanol) to give 16 mg of title compound with 12% of yield.

Workup

  1. additionwas added
  2. customReaction
  3. customThe solvent was evaporated
  4. customThe residue was purified by column chromatography (SiO2, cyclohexane/methylene chloride/methanol)

Sources & evidence

ORD record
ord-1160c39abd5e48689fd2bfd95cb6c8d4
Source dataset
uspto-grants-2014_09
Patent number
US08841453B2

Reaction notes

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