Pyridine → 6-(Tert-butoxycarbonyl)-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylic acid

HRID 1183816Notes

Reaction equation

HRID 1183816 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:19]2[C:11](=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([C:20]([O:22]C)=[O:21])=[CH:13]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN1CCN(C(Cl)=O)CC1.C(O)C=C.N1C=CC=CC=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:19]2[C:11](=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([C:20]([OH:22])=[O:21])=[CH:13]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7858Allyl AlcoholHCID 30169344-Methylpiperazine-1-carbonyl chloride monohydrochlorideHCID 151147736-tert-butyl 2-methyl 7,8-dihydropyrrolo[3,2-e]indole-2,6(3H)-dicarboxylate

Product 1

HCID 139953326-(Tert-butoxycarbonyl)-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylic acidYield 85.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

40 mg (0.27 mMol) of 5 was reacted overnight with 160 mg (0.81 mMol) of commercially available 4-methylpiperazine carbonylchloride hydrochloride in 17 mL of DCM with 1.7 mL of allylalcohol and 214 μL pyridine. The aolvent was evaporated and the crude compound was purified over silica with 5% MeOH/DCM as eluent to give 70 mg (40% yield) of 6. M+1=645.

Workup

  1. customThe aolvent was evaporated
  2. customthe crude compound was purified over silica with 5% MeOH/DCM as eluent

Sources & evidence

ORD record
ord-87e0ad6a712b4831a94f6b4f5ab16e82
Source dataset
uspto-grants-2014_03
Patent number
US08664407B2

Reaction notes

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