Potassium Carbonate → (R)-3-(2-Nitrophenylamino)piperidine-1-carboxylic acid tertbutyl ester

HRID 496663

Reaction equation

HRID 496663 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH2:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1F)([O-:17])=[O:16].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N+:15]([O-:17])=[O:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylate

Product 1

HCID 59073577(R)-3-(2-Nitrophenylamino)piperidine-1-carboxylic acid tertbutyl esterYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3(R)-amino-piperidine-1-carboxylic acid tert-butyl ester (137 mg, 0.69 mmol) and 2-nitrofluorobenzene (102 mg, 0.72 mmol), K2CO3 (100 mg) was heated at 110° C. for 12 hr. The mixture was diluted with CH2Cl2, filtered and concentrated. The residue was purified by chromatography (5% EtOAc in hexane) to give a yellow oil (134 mg, 61%). 1H-NMR (300 MHz, CDCl3) δ 8.20 (d, J=8.55 Hz, 1H, NH), 8.10 (d, J=7.20 Hz, 1H), 7.48 (t, 1H), 7.01 (d, J=8.30 Hz, 1H), 6.70 (t, 1H), 4.00 (broad, 1H), 3.75 (m, 1H), 3.60 (m, 1H), 3.20 (m, 2H), 2.10 (m, 1H), 1.82-1.60 (m, 3H), 1.43 (s, 9H) ppm; IR (film) 3357, 2967, 2935, 2858, 1692, 1620, 1572, 15508, 1423, 1372, 1266, 1230, 1154 cm−1; LRMS (calculated for C16H23N2O4) 321. found 321.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography (5% EtOAc in hexane)

Sources & evidence

ORD record
ord-74e5dc59a0cb4ff28b497afc4c6c5b6c
Source dataset
uspto-grants-2005_09
Patent number
US06946477B2

Linked notes

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