Triethylamine → tert-Butyl (2R)-2-[(4-benzylpiperazin-1-yl)carbonyl]piperazine-1-carboxylate

HRID 2371153Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2371153
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][C@@H:22]1[C:27](O)=[O:28])([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(N(CC)CC)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:27]([C@H:22]2[CH2:23][NH:24][CH2:25][CH2:26][N:21]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:28])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 759941-BenzylpiperazineHCID 2724699PyBOPHCID 24820285(2R)-1-(tert-Butoxycarbonyl)piperazine-2-carboxylic acid

Produkt 1

HCID 57656790tert-Butyl (2R)-2-[(4-benzylpiperazin-1-yl)carbonyl]piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-Benzylpiperazine (2.7 ml) and (2R)-1-BOC-piperazine-2-carboxylic acid (3.571 g) were suspended in DMF (150 ml) and stirred at 0° C. Triethylamine (4.33 ml) was added followed by PyBOP reagent (8.08 g). The mixture was allowed to warm to room temperature overnight, concentrated to approximately a third of the volume in vacuo and partitioned between brine (75 ml) and ethyl acetate (2×200 ml). Combined organic extracts were treated with saturated aqueous sodium bicarbonate (75 ml) and brine (75 ml), dried (sodium sulphate), concentrated in vacuo using high vacuum to remove DMF traces and purified by chromatography eluting with 0-15% methanol/dichloromethane. This gave tert-butyl (2R)-2-[(4-benzylpiperazin-1-yl)carbonyl]piperazine-1-carboxylate as a white glass (5.01 g).

Aufarbeitung

  1. temperatureto warm to room temperature overnight
  2. concentrationconcentrated to approximately a third of the volume in vacuo
  3. custompartitioned between brine (75 ml) and ethyl acetate (2×200 ml)
  4. additionCombined organic extracts were treated with saturated aqueous sodium bicarbonate (75 ml) and brine (75 ml)
  5. dry with materialdried (sodium sulphate)
  6. concentrationconcentrated in vacuo
  7. customto remove DMF traces
  8. custompurified by chromatography
  9. washeluting with 0-15% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-d90f1f5f2d524d9b9f6a792823c5ee5f
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710224B2

Notizen zur Reaktion

Wird geladen…