Diisopropylethylamine → (S)-tert-butyl (1-(3-nitropyridin-4-yl)piperidin-3-yl)carbamate

HRID 924369Notes

Reaction equation

HRID 924369 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:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[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:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:12]1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamateHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 67499955(S)-tert-butyl (1-(3-nitropyridin-4-yl)piperidin-3-yl)carbamateYield 98%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a 20 mL microwave vial containing 4-chloro-3-nitropyridine (Aldrich, 1.350 g, 8.515 mmol) and tert-butyl (3S)-piperidin-3-ylcarbamate (Combi-Blocks, 1.922 g, 9.597 mmol), 1-butanol (13.0 mL) was added, followed by DIPEA (2.213 g, 17.12 mmol). The reaction mixture was irradiated with microwaves at 130° C. for 1 h. The reaction mixture was then allowed to cool and concentrated under reduced pressure. The resulting residue was purified by flash chromatography on silica gel (0-100% EtOAc in hexanes) to give the sub-title compound as a yellow solid (2.69 g, 98%). LCMS calc. for C15H23N4O4 (M+H)+: m/z=323.2. found 323.2.

Workup

  1. additionwas added
  2. customThe reaction mixture was irradiated with microwaves at 130° C. for 1 h
  3. temperatureto cool
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by flash chromatography on silica gel (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c1ba2ee497c4490cbf3128eb7443f671
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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