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Acetic Acid → (2-(1-(2-Cyano-4-trifluoromethylphenyl)piperidin-4-ylamino)-ethyl)carbamic acid tert-butyl ester

HRID 842781
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 842781
[C:1]([C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1)#[N:2].[NH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].C(O)(=O)C.ClC(Cl)C.C([BH3-])#N.[Na+]>CO>[C:26]([O:25][C:24](=[O:30])[NH:23][CH2:22][CH2:21][NH:20][CH:16]1[CH2:17][CH2:18][N:13]([C:4]2[CH:5]=[CH:6][C:7]([C:9]([F:12])([F:11])[F:10])=[CH:8][C:3]=2[C:1]#[N:2])[CH2:14][CH2:15]1)([CH3:29])([CH3:27])[CH3:28]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 187201N-BOC-ethylenediamineHCID 5003444Sodium cyanoborohydrideHCID 22615393N-(2-Cyano-4-trifluoromethylphenyl)-4-piperidone

Produkt 1

HCID 18727097
(2-(1-(2-Cyano-4-trifluoromethylphenyl)piperidin-4-ylamino)-ethyl)carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 25 (535 mg, 1.99 mmol), 1 (335 mg, 2.09 mmol), and acetic acid (629 mg, 10.48 mmol) in methanol(2 mL)/dichloroethane(1 mL) was treated with sodium cyanoborohydride (130 mg, 2.06 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue dissolved in dichloromethane and sodium carbonate solution. The aqueous layer was extracted with two additional portions of dichloromethane and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. PCTLC (SiO2, 4 mm, 10% EtOH-90% CHCl3) afforded the title compound (26).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in dichloromethane
  3. extractionThe aqueous layer was extracted with two additional portions of dichloromethane
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d87d1e5e969244feadcc07b3064c15af
Quelldatensatz
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06376503B1

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