1-(2-Chloroethyl)pyrrolidine → Tert-butyl 4-(2-pyrrolidin-1-ylethoxymethyl)piperidine-1-carboxylate

HRID 928573Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 928573
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.Cl[CH2:17][CH2:18][N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O.C(Cl)Cl>[N:19]1([CH2:18][CH2:17][O:1][CH2:2][CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Komponenten

6

Edukt 2

HCID 816691-(2-Chloroethyl)pyrrolidineHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Produkt 1

HCID 89579709Tert-butyl 4-(2-pyrrolidin-1-ylethoxymethyl)piperidine-1-carboxylateAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 22272177Toluene waterLösungsmittel

Versuchsvorschrift

Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (5 g, 0.023 moles), 1-(2-chloroethyl)pyrrolidine (7.82 g, 0.046 moles) and tetrabutylammonium bromide (0.741 g, 2.3 mmol) were heated in toluene/water (1:1, 60 mL) to 90° C. overnight. The reaction mixture was diluted with DCM (100 mL), washed with water (100 mL), dried over Na2SO4 and concentrated at reduced pressure. The resulting residue was purified by flash chromatography, eluting with a gradient from DCM to 90/10 DCM/methanol to afford tert-butyl 4-(2-pyrrolidin-1-ylethoxymethyl)piperidine-1-carboxylate (5.28 g). LCMS [M+H]+=313.2

Aufarbeitung

  1. washwashed with water (100 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated at reduced pressure
  4. customThe resulting residue was purified by flash chromatography
  5. washeluting with a gradient from DCM to 90/10 DCM/methanol

Quellen und Nachweise

ORD-Eintrag
ord-36c7177e2cc342109c23a7e796fd421f
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290511B2

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