Water → HCID 89618826, compound

HRID 1502085Notes

Reaction equation

HRID 1502085 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)=[O:4].[OH:14][CH2:15][C@H:16]1[NH:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1.CCN(C(C)C)C(C)C.O>C1COCC1>[OH:14][CH2:15][C@H:16]1[N:21]([CH2:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=2)=[O:4])[CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-oneHCID 81531DiisopropylethylamineHCID 24820294tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate

Product 1

HCID 89618826HCID 89618826, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Bromo-1-(3-nitrophenyl)ethanone (1.01 g, 4.14 mmol) was dissolved in THF (20 mL) and added (S)-tert-butyl 3-(hydroxymethyl)piperazine-1-carboxylate (1.074 g, 4.97 mmol) followed by Hunig's base (1.45 mL, 8.28 mmol) then stirred at room temperature overnight. The reaction was poured into water and extracted with ETOAC (2×). The organic layer was separated, dried over Na2SO4, filtered and concentrated. The product was purified by chromatography through a 120 g ISCO Redi-sep column eluting with 0-70% ethyl acetate/hexane to yield the title compound.

Workup

  1. extractionextracted with ETOAC (2×)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by chromatography through a 120 g ISCO Redi-sep column
  7. washeluting with 0-70% ethyl acetate/hexane

Sources & evidence

ORD record
ord-79be257c5b834b9aa947f30bcd31cf32
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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