Trimethylsilyldiazomethane → 1-Tert-butyl 3-methyl 3-aminopyrrolidine-1,3-dicarboxylate

HRID 2191562Notes

Reaction equation

HRID 2191562 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([NH2:16])([C:13]([OH:15])=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[CH3:17][O:14][C:13]([C:10]1([NH2:16])[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]1)=[O:15]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 247303163-Amino-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid

Product 1

HCID 576862811-Tert-butyl 3-methyl 3-aminopyrrolidine-1,3-dicarboxylateYield 102.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

In a round-bottomed flask 3-aminopyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (0.20 g, 0.87 mmol) was dissolved in dichloromethane (3.2 mL) and MeOH (1.6 mL). (Trimethylsilyl)diazomethane (2.0 M in hexanes, 0.75 mL, 1.5 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 5 h. The reaction mixture was quenched with a small portion of acetic acid and concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with saturated aqueous Na2CO3. The aqueous layer was extracted with dichloromethane and the combined organics were dried over Na2SO4 and concentrated to afford 0.218 g of 3-amino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester as a light yellow oil.

Workup

  1. customThe reaction mixture was quenched with a small portion of acetic acid
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with saturated aqueous Na2CO3
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. dry with materialthe combined organics were dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-22128106116043b78146309240c48f0e
Source dataset
uspto-grants-2012_12
Patent number
US08329699B2

Reaction notes

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