Triethylamine → (3S,4S)-4-(4-Bromo-2-nitro-phenylamino)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

HRID 1670634Notes

Reaction equation

HRID 1670634 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH2:14])[C@@H:10]([OH:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:16][C:17]1[CH:18]=[CH:19][C:20](F)=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=1.C(N(CC)CC)C>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:20]2[CH:19]=[CH:18][C:17]([Br:16])=[CH:22][C:21]=2[N+:23]([O-:25])=[O:24])[C@@H:10]([OH:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 58413001HCID 58413001, compound

Product 1

HCID 67335296(3S,4S)-4-(4-Bromo-2-nitro-phenylamino)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl esterYield 110.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Heat a mixture of (3S,4S)-4-amino-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.035 mol, 7.5 g), 5-bromo-2-fluoronitrobenzene (0.038 mol, 8.48 g) and triethyl amine (0.073 mol, 7.44 g) in ethyl acetate (250 mL) to reflux for 16 h. Cool the reaction mixture to room temperature, dilute with ethyl acetate and wash with water and brine. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate to obtain the title compound (16.16 g, crude).

Workup

  1. temperatureHeat
  2. temperatureto reflux for 16 h
  3. washwash with water and brine
  4. dry with materialDry the organic layer over anhydrous sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-c5b4ba77c0fc4e5091ee49cdb69e5e7b
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

Loading…