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

HRID 383772

Reaction equation

HRID 383772 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.CNOC.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,O-dimethylhydroxylamine hydrochloride (1.17 g, 12.0 mmol), and triethylamine (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-19a. 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-d65a7faf4e0d4896b400aacbe02f87f1
Source dataset
uspto-grants-2013_02
Patent number
US08367679B2

Linked notes

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