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

HRID 1465708Notes

Reaction equation

HRID 1465708 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH3:18][NH:19][O:20][CH3:21].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.ClCCl>[CH3:21][O:20][N:19]([CH3:18])[C:14]([CH:10]1[CH2:11][CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:9]1)=[O:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27356471-((Tert-butoxy)carbonyl)piperidine-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 22248320Tert-butyl 3-[methoxy(methyl)carbamoyl]piperidine-1-carboxylateYield 124.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To the solution of 1-Boc-piperidine-3-carboxylic acid (6.9 g, 30 mmol) in DMF (10 mL) and dichloromethane (40 mL) were added N,O-dimethylhydroxylamine hydrochloride (3.22 g, 33 mmol), HATU (12 g, 31.5 mmol) and triethylamine (9 mL). The reaction mixture was stirred overnight. After most of the solvent was removed and diluted with EtOAc, the organic layer was washed with water and brine, Dried and evaporation to give 10.2 g of crude product as light yellow oil.

Workup

  1. customAfter most of the solvent was removed
  2. additiondiluted with EtOAc
  3. washthe organic layer was washed with water and brine
  4. customDried
  5. customevaporation

Sources & evidence

ORD record
ord-48069e725f3d460eb11457ea8c33ec3a
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

Loading…