Imidazole → Benzyl 4-(2-iodoethyl)piperidine-1-carboxylate

HRID 260131

Reaktionsgleichung

Reaktionsgleichung von HRID 260131
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18]O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:44]I>>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][I:44])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 13971210Benzyl 4-(2-hydroxyethyl)piperidine-1-carboxylate

Produkt 1

HCID 14600697Benzyl 4-(2-iodoethyl)piperidine-1-carboxylate

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 3-2(263 g, 116 mmol) was treated with triphenylphosphine (33.5 g, 128 mmol), imidazole (11.9 g, 175 mmol) and cooled to 0° C. Iodine (32.4 g, 128 mmol) was added and the ice bath was removed. The reaction was filtered into a separatory funnel and the solution was washed with H2O and brine, dried over MgSO4 and concentrated. The residue was chromatographed (10% EtOAc/Hexanes) to give 3-3 as a colorless oil. Rf (20% EtOAc/Hexanes) 0.56 1H NMR (300 MHz, CDCl3) δ 7.4-7.1 (m, 5H), 5.2-5.05 (bs, 2H), 4.3-4.1 (bs, 2H), 3.2 (t, 2H), 2.8 (bs, 2H), 1.8-1.5 (m, 5H), 1.15 (m, 2H). ##STR31## 2(N-t-Butyloxycarbonylaminopiperidin-4-yl)ethanol (4-1)

Aufarbeitung

  1. customthe ice bath was removed
  2. filtrationThe reaction was filtered into a separatory funnel
  3. washthe solution was washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed (10% EtOAc/Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c28c39753c9847c4954ff6b09d0aa8be
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05525617

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