Triethylamine → tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

HRID 2202147Notes

Reaction equation

HRID 2202147 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:18][NH:19][O:20][CH3:21].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:21][O:20][N:19]([CH3:18])[C:14]([CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1)=[O:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 11065582tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (Aldrich, 6.0 g, 26.2 mmol), N,O-dimethylhydroxylamine hydrochloride (3.06 g, 31.4 mmol), DMAP (3.20 g, 26.2 mmol), and triethyl amine (4.74 mL, 34 mmol) in DCM (200 mL) was stirred at room temperature overnight. The mixture was washed with saturated aqueous KHSO4 and brine. The organic layer was dried (MgSO4) and the solvent was removed. The crude material was directly used in the next step.

Workup

  1. washThe mixture was washed with saturated aqueous KHSO4 and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-b8ce5187a9bc42f7a4283da38ac899ac
Source dataset
uspto-grants-2016_06
Patent number
US09365539B2

Reaction notes

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