Potassium Carbonate → Benzyl 4-((3-(((tert-butoxycarbonyl)amino)(phenyl)methyl)phenoxy)methyl)-piperidine-1-carboxylate

HRID 332712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 332712
[C:1]([O:5][C:6](=[O:22])[N:7](C1C=CC=C(O)C=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].S([O:39][CH2:40][CH:41]1[CH2:46][CH2:45][N:44]([C:47]([O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:48])[CH2:43][CH2:42]1)(C1C=CC(C)=CC=1)(=O)=O>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:7][CH:8]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[O:39][CH2:40][CH:41]1[CH2:42][CH2:43][N:44]([C:47]([O:49][CH2:50][C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)=[O:48])[CH2:45][CH2:46]1)=[O:22])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 218920784-(Toluene-4-sulfonyloxymethyl)-piperidine-1-carboxylic acid benzyl esterHCID 86676908Tert-butyl(3-hydroxyphenyl)(phenyl)methylcarbamate

Produkt 1

HCID 71093338Benzyl 4-((3-(((tert-butoxycarbonyl)amino)(phenyl)methyl)phenoxy)methyl)-piperidine-1-carboxylateAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of tert-butyl(3-hydroxyphenyl)(phenyl)methylcarbamate. (the second eluting isomer from Chiral Example 1 Step 4, 1.00 g, 3.34 mmol) in DMF (15 mL), was added potassium carbonate (0.554 g, 4.01 mmol). The reaction mixture was stirred for 10 minutes, and benzyl 4-((tosyloxy)methyl)piperidine-1-carboxylate (prepared according to Bioorganic & Medicinal Chemistry Letters, 20(1), 380-382; 2010, which is incorporated herein by reference in its entirety, 1.48 g, 3.67 mmol) added. The reaction mixture was heated at 60° C. for 2 days followed by 80° C. for 5 days. The reaction mixture was diluted with ethyl acetate and washed with water and saturated brine (×2). The organic phase was dried with anhydrous magnesium sulfate, and the solvent evaporated at reduced pressure. The crude material was purified by silica gel chromatography eluting with 100% iso-hexane to 50% ethyl acetate in iso-hexane to afford the title compound (1.12 g, 63%).

Aufarbeitung

  1. additionadded
  2. waitfollowed by 80° C. for 5 days
  3. washwashed with water and saturated brine (×2)
  4. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
  5. customthe solvent evaporated at reduced pressure
  6. customThe crude material was purified by silica gel chromatography
  7. washeluting with 100% iso-hexane to 50% ethyl acetate in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-e43ef9fa239c4091ade8575e024a83cd
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877774B2

Notizen zur Reaktion

Wird geladen…