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Benzoic Acid → (trans)-Benzyl 4-(benzoyloxy)-3-fluoropiperidine-1-carboxylate

HRID 2035648
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2035648
[F:1][C@H:2]1[C@@H:7]([OH:8])[CH2:6][CH2:5][N:4]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:38](O)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:38]([O:8][C@@H:7]1[CH2:6][CH2:5][N:4]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3][C@H:2]1[F:1])(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 52324487(3R,4S)-Benzyl 3-fluoro-4-hydroxypiperidine-1-carboxylate

Produkt 1

HCID 131731019(trans)-Benzyl 4-(benzoyloxy)-3-fluoropiperidine-1-carboxylateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Non-racemic (cis)-benzyl 3-fluoro-4-hydroxypiperidine-1-carboxylate (Peak 1 of Example 94, Step 3D; 0.306 g, 1.21 mmol) was treated with triphenylphosphine (0.475 g, 1.81 mmol) and benzoic acid (0.221 g, 1.81 mmol) and the solids were dissolved in THF (5 mL), then cooled to 0° C. The solution was treated dropwise with diisopropyl azodicarboxylate (0.357 mL, 1.81 mmol) dissolved in THF (1 mL). The solution was warmed to ambient temperature with a bath and stirred for 7 days, then concentrated in vacuo. The residue was dissolved in CH2Cl2 and washed with saturated NH4Cl, water, 50% saturated NaHCO3, dried over Na2SO4 and concentrated in vacuo to a colorless oil. The oil was chromatographed on SiO2 eluting with 1:12 acetone/hexanes. The desired fraction was isolated to provide the desired product as a colorless oil (385 mg).

Aufarbeitung

  1. temperatureThe solution was warmed to ambient temperature with a bath
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with saturated NH4Cl, water, 50% saturated NaHCO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo to a colorless oil
  7. customThe oil was chromatographed on SiO2 eluting with 1:12 acetone/hexanes
  8. customThe desired fraction was isolated

Quellen und Nachweise

ORD-Eintrag
ord-bdb257b987a6429ab436a52ea7295681
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08575145B2

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