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N-Boc-3-mesyloxypiperidine → 3-(1-Chloroisoquinolin-6-yloxy)piperidine-1-carboxylic acid tert-butyl ester

HRID 1435990
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1435990
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH2:23][CH:22](OS(C)(=O)=O)[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].CCN(P1(N(C)CCCN1)=NC(C)(C)C)CC>C(#N)C>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH2:23][CH:22]([O:12][C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[C:2]([Cl:1])=[N:3][CH:4]=[CH:5]3)[CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]
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Komponenten

5

Edukt 3

HCID 568122N-Boc-3-mesyloxypiperidineHCID 199900182-tert-butylimino-N,N-diethyl-1-methyl-1,3,2lambda5-diazaphosphinan-2-amineHCID 1357421771-chloro-2H-isoquinolin-6-one

Produkt 1

HCID 866129773-(1-Chloroisoquinolin-6-yloxy)piperidine-1-carboxylic acid tert-butyl esterAusbeute 29,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

The 1-chloro-6-methoxyisoquinoline was prepared as described in WO 00/24718 (Akzo Nobel N.V.). Alternatively it can be prepared from 3-methoxybenzaldehyde using the same procedure as in Example 15A (for the synthesis of 1-chloro-6-methoxy-7-methyl-isoquinoline). The 1-chloro-6-methoxyisoquinoline is demethylated according to the procedure described in WO 00/24718 to afford 1-chloro-6-hydroxyisoquinoline. A suspension of 1-chloro-6-hydroxyisoquinoline (0.18 g, 1 mmol), 3-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester (336 mg, 1.2 mmol) and 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine on polystyrene (500 mg, ˜2.2mmol/g loading) in acetonitrile (4 ml) were heated at 120° C. over a period of 900 seconds using the microwave. The excess supported reagent was removed by filtration, washing with methanol, and the filtrate evaporated to dryness under reduced pressure. Since the reaction had not gone to completion, the above procedure was repeated. Purification of the crude material was achieved by chromatography on silica (eluent: 0-25% ethyl acetate in heptane) to afford 3-(1-chloroisoquinolin-6-yloxy)piperidine-1-carboxylic acid tert-butyl ester (106 mg), El-MS: m/z=363.7 [M+H]+.

Aufarbeitung

  1. customwas removed by filtration
  2. washwashing with methanol
  3. customthe filtrate evaporated to dryness under reduced pressure
  4. customPurification of the crude material

Quellen und Nachweise

ORD-Eintrag
ord-04dfb89f95bf471b8ebd5aef018a60bc
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07618985B2

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