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Pyrazole → (2R,5R)-4-Benzyl-2-methyl-5-pyrazol-1-ylmethyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 1475444
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1475444
CS(OS(C)(=O)=O)(=O)=O.[C:10]([O:14][C:15]([N:17]1[CH2:22][C@H:21]([CH2:23]O)[N:20]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:19][C@H:18]1[CH3:32])=[O:16])([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C.[NH:40]1[CH:44]=[CH:43][CH:42]=[N:41]1>C(Cl)Cl>[C:10]([O:14][C:15]([N:17]1[CH2:22][C@H:21]([CH2:23][N:40]2[CH:44]=[CH:43][CH:42]=[N:41]2)[N:20]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:19][C@H:18]1[CH3:32])=[O:16])([CH3:13])([CH3:12])[CH3:11]
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Komponenten

6

Edukt 4

HCID 1048PyrazoleHCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 70980613tert-butyl (2R,5R)-4-benzyl-5-(hydroxymethyl)-2-methylpiperazine-1-carboxylate

Produkt 1

HCID 70980646(2R,5R)-4-Benzyl-2-methyl-5-pyrazol-1-ylmethyl-piperazine-1-carboxylic acid tert-butyl esterAusbeute 64,8 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of methanesulfonic anhydride (0.65 g, 3.72 mmol) in DCM (5 mL) was added slowly to a solution of (2R,5R)-4-benzyl-5-hydroxymethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester (1.08 g, 3.38 mmol) and triethylamine (1.42 mL, 1.02 g, 10.1 mmol) in DCM (10 mL) with stirring under nitrogen and external ice bath cooling. Stirring was continued at 0° C. for 2 h then pyrazole (0.3 g, 4.4 mmol) was added in one portion. Stirring at 20° C. was continued for 18 h, then mixture was partitioned between saturated aqueous NaHCO3 (40 mL) and DCM (3×20 mL). Combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give an oil. Chromatography (SiO2; gradient elution with 0-40% Et2O in 40-60 petroleum ether) gave the title compound (0.811 g) as an oil. MS: [M+H]+=371.

Aufarbeitung

  1. temperatureexternal ice bath cooling
  2. stirringStirring
  3. stirringStirring at 20° C.
  4. waitwas continued for 18 h
  5. custommixture was partitioned between saturated aqueous NaHCO3 (40 mL) and DCM (3×20 mL)
  6. dry with materialCombined organic extracts were dried (Na2SO4)
  7. customevaporated in vacuo
  8. customto give an oil
  9. washChromatography (SiO2; gradient elution with 0-40% Et2O in 40-60 petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-565f4a8c38d94ac8a07d6f5dc35be848
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09018214B2

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