1,1'-Carbonyldiimidazole → [1-Methyl-2-[[(3-methyl-1-(phenylmethyl)-3-pyrrolidinyl)methyl]amino]-2-oxoethyl]carbamic acid, 1,1-dimethylethyl ester

HRID 232054Notes

Reaction equation

HRID 232054 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:26][C:27]1([CH2:39][NH2:40])[CH2:31][CH2:30][N:29]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:28]1>C(#N)C>[CH3:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:11]([NH:40][CH2:39][C:27]1([CH3:26])[CH2:31][CH2:30][N:29]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:28]1)=[O:13]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 85082Tert-butoxycarbonylalanineHCID 14235022(1-Benzyl-3-methylpyrrolidin-3-yl)methanamine

Product 1

HCID 14555506[1-Methyl-2-[[(3-methyl-1-(phenylmethyl)-3-pyrrolidinyl)methyl]amino]-2-oxoethyl]carbamic acid, 1,1-dimethylethyl esterYield 90.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 14.1 g (75 mmole) of t-butoxycarbonyl-L-alanine in 135 ml of dry acetonitrile was treated with 12.5 g (77 mmol) of 1,1'-carbonyldiimidazole. After stirring at room temperature for one hour and gas evolution had ceased, the reaction mixture was heated at 60° for one hour cooled to room temperature and treated with 14.2 g (70 mmol) of 3-methyl-1-(phenylmethyl)-3-pyrrolidinemethanamine. The reaction mixture was stirred at room temperature for 18 hours and the solvent was removed in vacuo. The residue was partitioned between ethyl acetate/water and the organic layer was separated, washed with water, dried (MgSO4), and evaporated in vacuo to give 23.9 g of the title compound.

Workup

  1. temperaturethe reaction mixture was heated at 60° for one hour
  2. temperaturecooled to room temperature
  3. stirringThe reaction mixture was stirred at room temperature for 18 hours
  4. customthe solvent was removed in vacuo
  5. customThe residue was partitioned between ethyl acetate/water
  6. customthe organic layer was separated
  7. washwashed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-96e2d52902a34a25b2fe854462ab72ef
Source dataset
uspto-grants-1989_07
Patent number
US04851418

Reaction notes

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