3,4,5-Trimethoxybenzoic Acid → N-Boc-pyrrolidine

HRID 1992746Notes

Reaction equation

HRID 1992746 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1CNCC(C)=CC1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N1CCC[C@@H]1CC(O)=O)=O)(C)(C)C.COC1C=C(C=C(OC)C=1OC)C(O)=O.CN(CCCN=C=NCC)C.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 83573,4,5-Trimethoxybenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 688606boc-d-beta-homoprolineHCID 68683013HCID 68683013, compound

Product 1

HCID 643455N-Boc-pyrrolidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Experimental condition analogous to Example 22 were used with 2-(R)-[(2-methyl-3-phenyl-allylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (prepared according to the scheme 13) were used with 2-(R)-carboxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester) 0.5 g (1.51 mmol), 3,4,5-trimethoxy benzoic acid 0.38 g (1.8 mmol), triethylamine 0.1 ml, 1-(dimethylaminopropyl)-3-ethylcarbodiimide 0.43 g (2.2 mmol), and 1-hydroxybenzotriazole 0.2 g (1.5 mmol) in 10 ml DCM. The reaction yielded 0.46 g of 2-(R){[2-methyl-3-phenyl-allyl)-3,4,5-trimethoxy-benzoyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester. After BOC deprotection analogous to the Example 13, the compound was transformed to the HCl salt, 0.35 g of a white solid was obtained. Yield: 50%

Workup

  1. customprepared

Sources & evidence

ORD record
ord-94bedcc83474421bb17e9e926edb093f
Source dataset
uspto-grants-2010_01
Patent number
US07649011B2

Reaction notes

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