Triethylamine → 3-[{N-(tert-butoxycarbonyl)glycyl)aminomethyl]-1-(4-chlorobenzyl)pyrrolidine

HRID 279280Notes

Reaction equation

HRID 279280 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH2:4]1.CCN(CC)CC.[C:23]([O:27][C:28]([NH:30][CH2:31][C:32](O)=[O:33])=[O:29])([CH3:26])([CH3:25])[CH3:24].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>ClCCl>[C:23]([O:27][C:28]([NH:30][CH2:31][C:32]([NH:1][CH2:2][CH:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[CH2:4]1)=[O:33])=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 184262513-(Aminomethyl)-1-(4-chlorobenzyl)pyrrolidine

Product 1

HCID 184262553-[{N-(tert-butoxycarbonyl)glycyl)aminomethyl]-1-(4-chlorobenzyl)pyrrolidineYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-(aminomethyl)-1-(4-chlorobenzyl)pyrrolidine (860 mg, 3.8 mmol), Et3N (5.7 mmol), N-tert-butoxycarbonylglycine (704 mg), EDCI (594 mg), HOBt (673 mg), and dichloromethane (20 mL) was stirred at room temperature for 15 h. Dichloromethane (50 mL) was added and the solution was washed with 2 N NaOH solution (50 mL×2), dried over anhydrous sodium sulfate, filtered, and concentrated to afford 3-[{N-(tert-butoxycarbonyl)glycyl)aminomethyl]-1-(4-chlorobenzyl)pyrrolidine (1.31 g, 90%).

Workup

  1. washthe solution was washed with 2 N NaOH solution (50 mL×2)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d3838a975cd147d2882d5165eac4447b
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Reaction notes

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