4-Methylmorpholine → Tert-butyl 3-[(2-acetylhydrazino)carbonyl]pyrrolidine-1-carboxylate

HRID 383768Notes

Reaction equation

HRID 383768 reaction equation
ClC(OCC(C)C)=O.[C:9]([O:13][C:14]([N:16]1[CH2:20][CH2:19][CH:18]([C:21]([OH:23])=O)[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].CN1CCOCC1.[C:31]([NH:34][NH2:35])(=[O:33])[CH3:32]>C1COCC1>[C:31]([NH:34][NH:35][C:21]([CH:18]1[CH2:19][CH2:20][N:16]([C:14]([O:13][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:15])[CH2:17]1)=[O:23])(=[O:33])[CH3:32]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 14039AcetohydrazideHCID 62365Isobutyl chloroformateHCID 27605291-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acid

Product 1

HCID 67347085Tert-butyl 3-[(2-acetylhydrazino)carbonyl]pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Isobutyl chloroformate (152 μL, 1.16 mmol) was added to a stirred solution of 1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (237 mg, 1.10 mmol) and 4-methylmorpholine (182 μL, 1.65 mmol) in THF (5.50 mL) at −78° C. After 15 min, added acetic hydrazide (2.0 mg, 1.10 mmol), and the resulting mixture was warmed slowly to rt. After 1 h, the reaction mixture was quenched with 0.5 M HCl and extracted with EtOAc. The combined organics were dried (sodium sulfate) and concentrated in vacuo to afford the title compound i-8a. m/z (ES) 272 (MH)+.

Workup

  1. waitAfter 1 h
  2. customthe reaction mixture was quenched with 0.5 M HCl
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organics were dried (sodium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a3c471be40a04c74ab5aace1dff35fb7
Source dataset
uspto-grants-2013_02
Patent number
US08367679B2

Reaction notes

Loading…