Triethylamine → (3S,4S)-tert-butyl 3-(4-bromo-2-nitrophenylamino)-4-hydroxypyrrolidine-1-carboxylate

HRID 1670619Notes

Reaction equation

HRID 1670619 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:23][C@H:22]([OH:24])[C@@H:21]([NH:25]CC2C=CC=CC=2)[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>C(OCC)(=O)C>[C:12]([O:16][C:17]([N:19]1[CH2:23][C@H:22]([OH:24])[C@@H:21]([NH:25][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[N+:9]([O-:11])=[O:10])[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 11277777tert-butyl (3S,4S)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 67333783(3S,4S)-tert-butyl 3-(4-bromo-2-nitrophenylamino)-4-hydroxypyrrolidine-1-carboxylateYield 94.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-bromo-4-fluoro-3-nitrobenzene (0.125 mol, 26.0 g) in ethyl acetate (300 mL) add (3S,4S)-3-benzylamino-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (0.113 mol, 23.0 g) and triethylamine (0.339 mol, 35.0 g), reflux for 14 h, cool to room temperature, and wash with water and brine. Dry over anhydrous sodium sulfate, evaporate the solvent, and purify by flash column chromatography to give the title compound as a yellow solid (43.0 g, 90%). APCI MS m/z 403 [M+H]+.

Workup

  1. temperaturereflux for 14 h
  2. washwash with water and brine
  3. dry with materialDry over anhydrous sodium sulfate
  4. customevaporate the solvent
  5. custompurify by flash column chromatography

Sources & evidence

ORD record
ord-cc52c384dabf4d5989895f7a18c15a44
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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