1,2-Dichloroethane → Methyl 3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylate

HRID 1255963Notes

Reaction equation

HRID 1255963 reaction equation
[CH2:1](Cl)[CH2:2]Cl.[CH:5]1[CH:6]=[CH:7][C:8]2[N:13](O)N=N[C:9]=2[CH:10]=1.C(Cl)Cl.[C:18]([O:22][C:23](=[O:31])[C:24]1[CH:29]=CC(N)=CC=1)(C)(C)C.C[N:33](C=O)C>[Cu](Cl)Cl>[CH2:1]1[C:9]2=[C:10]3[C:5](=[CH:6][CH:7]=[C:8]2[NH:13][CH2:2]1)[NH:33][C:24]([C:23]([O:22][CH3:18])=[O:31])=[CH:29]3

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 6344DichloromethaneHCID 757711-HydroxybenzotriazoleHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl ester

Product 1

HCID 15480266Methyl 3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 24014Cupric ChlorideCatalyst

Procedure

1.5 grams (3.77 mMoles) of Fmoc-citruline were dissolved in 3 mL of DMF in a round bottom flask to which was added 0.87 grams (4.5 mMoles) of EDC, 0.61 grams (4.5 mMoles) of HOBt. 6 mL of DCM were then added followed by the addition 0.88 grams (4.5 mMoles) of t-butyl-4-aminobenzoate and a catalytic amount of copper chloride. The reaction mixture was allowed to stir overnight The solvents were evaporated and the crude product purified over silica gel with 5 to 10% MeOH in DCM to give 2 grams of 4 in 92% yield. M+1=574

Workup

  1. customwere evaporated
  2. customthe crude product purified over silica gel with 5 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-1e6d4896c0cb4012b6cb5a86bfccf778
Source dataset
uspto-grants-2013_06
Patent number
US08461117B2

Reaction notes

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