Diisopropylethylamine → Benzyl [(3S)-1-(3-nitropyridin-4-yl)piperidin-3-yl]carbamate

HRID 924362Notes

Reaction equation

HRID 924362 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:12]1.CCN(C(C)C)C(C)C>C(O)CCC>[N+:8]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[N:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:12]1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514175Benzyl (3S)-piperidin-3-ylcarbamateHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 86726855Benzyl [(3S)-1-(3-nitropyridin-4-yl)piperidin-3-yl]carbamateYield 96%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a 20 mL microwave vial containing 4-chloro-3-nitropyridine (Aldrich, 1.373 g, 8.660 mmol) and benzyl (3S)-piperidin-3-ylcarbamate (MolBridge, 2.077 g, 8.865 mmol), 1-butanol (10.0 mL) was added followed by DIPEA (1.836 g, 14.20 mmol). The mixture was irradiated with microwaves at 130° C. for 1 h. The mixture was then concentrated under reduced pressure, and the resulting residue was purified by flash chromatography on silica gel (0-30% MeOH in DCM) to give the sub-title compound as a yellow solid (2.96 g, 96%). LCMS calc. for C18H21N4O4 (M+H)+: m/z=357.2. found 357.1.

Workup

  1. additionwas added
  2. customThe mixture was irradiated with microwaves at 130° C. for 1 h
  3. concentrationThe mixture was then concentrated under reduced pressure
  4. customthe resulting residue was purified by flash chromatography on silica gel (0-30% MeOH in DCM)

Sources & evidence

ORD record
ord-ae04b6b259954c30bd00bf7d1498f319
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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