Triethylamine → Tert-butyl 3-[methoxy(methyl)carbamoyl]pyrrolidine-1-carboxylate

HRID 1260289Notes

Reaction equation

HRID 1260289 reaction equation
CN([C:4]([O:8][N:9]1N=NC2C=CC=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([O:29][C:30]([N:32]1[CH2:36][CH2:35][CH:34]([C:37]([OH:39])=O)[CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].Cl.CONC.C(N(CC)CC)C>C(Cl)Cl>[CH3:4][O:8][N:9]([CH3:10])[C:37]([CH:34]1[CH2:35][CH2:36][N:32]([C:30]([O:29][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:31])[CH2:33]1)=[O:39]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27605291-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

HATU (4.56 g, 12.0 mmol) was added to 1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (2.15 g, 10.0 mmol), N-methoxy-N-methylamine hydrochloride (1.16 g, 12.0 mmol), and triethylamine (4.18 mL, 30.0 mmol) in DCM (50.0 mL), and the resulting mixture was allowed to stir at rt. After 12 h, the reaction mixture was diluted with DCM, and the combined organics were washed with water and brine, dried (sodium sulfate) and concentrated in vacuo to afford the title compound i-18a. m/z (ES) 259 (MH)+.

Workup

  1. washthe combined organics were washed with water and brine
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d6845f5a4e8c46deb65e27cf82d35e69
Source dataset
uspto-grants-2013_06
Patent number
US08470819B2

Reaction notes

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