Methanamine, N-methoxy-, hydrochloride (1:1) → Tert-butyl 3-[methoxy(methyl)carbamoyl]pyrrolidine-1-carboxylate

HRID 253547

Reaction equation

HRID 253547 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:17][NH:18][O:19][CH3:20].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH3:20][O:19][N:18]([CH3:17])[C:13]([CH:10]1[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9]1)=[O:15]

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27605291-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acid

Product 1

HCID 57419605Tert-butyl 3-[methoxy(methyl)carbamoyl]pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (4.00 g, 18.6 mmol), N,O-dimethylhydroxylamine hydrochloride (1.69 g, 17.4 mmol), and DIEA (7.5 mL, 41.8 mmol) in CH2Cl2 (80 mL) was added solid EDC.HCl (4.00 g, 20.9 mmol). The mixture was stirred at rt for 18 h and concentrated under reduced pressure. The residue was taken up in ether (175 mL), washed with 5% aq HCl (2×50 mL) and satd aq NaHCO3 (50 mL), and dried over MgSO4. Removal of the solvent left tert-butyl 3-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (3.16 g, 65%) as an oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed with 5% aq HCl (2×50 mL)
  3. dry with materialdried over MgSO4
  4. customRemoval of the solvent
  5. waitleft tert-butyl 3-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (3.16 g, 65%) as an oil

Sources & evidence

ORD record
ord-51b8c79eb25f4cb388926ab69e6be43e
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Linked notes

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