Ethyl formate → 1-Boc-4-[(1-methyl-4-piperidyl)methyl]piperidine

HRID 1869631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1869631
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:27](OCC)=O>O1CCCC1>[CH3:27][N:1]1[CH2:2][CH2:3][CH:4]([CH2:7][CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]2)[CH2:5][CH2:6]1

Komponenten

5

Edukt 3

HCID 8025Ethyl formateHCID 21226445Aluminium lithium hydrideHCID 497611974-Piperidin-4-ylmethyl-piperidine-1-carboxylic acid t-butyl ester

Produkt 1

HCID 688889221-Boc-4-[(1-methyl-4-piperidyl)methyl]piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1,1-Dimethylethyl 4-(4-piperidinylmethyl)-1-piperidinecarboxylate (may be prepared as described in Description 2) (1.5 g), and LiAlH4 (26.6 ml of 1M solution in tetrahydrofuran) were combined in tetrahydrofuran (10 ml) and the reaction mixture stirred at room temperature for 10 min before cooling to 0° C. in an ice/water bath. Ethyl formate (5 ml) was then added dropwise. The reaction was then quenched with 3 N sodium hydroxide solution. The solid precipitate formed was filtered and washed with more tetrahydrofuran. The combined organics were dried over Na2SO4, and evaporated to give the title compound (D18) (1.1 g).

Aufarbeitung

  1. temperaturebefore cooling to 0° C. in an ice/water bath
  2. customThe reaction was then quenched with 3 N sodium hydroxide solution
  3. customThe solid precipitate formed
  4. filtrationwas filtered
  5. washwashed with more tetrahydrofuran
  6. dry with materialThe combined organics were dried over Na2SO4
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-7cdeab6b0ba04e769d77c58f584344a8
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638631B2

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