Triethylamine → 1,1-Dimethylethyl 4-{[1-(cyclopropylmethyl)-4-piperidinyl]methyl}-1-piperidinecarboxylate

HRID 1869627Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1869627
[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.[CH2:21]1[CH:23]([CH:24](O)C#N)[CH2:22]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH:23]1([CH2:24][N:1]2[CH2:2][CH2:3][CH:4]([CH2:7][CH:8]3[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]3)[CH2:5][CH2:6]2)[CH2:21][CH2:22]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 113893592-Cyclopropyl-2-hydroxyacetonitrileHCID 497611974-Piperidin-4-ylmethyl-piperidine-1-carboxylic acid t-butyl ester

Produkt 1

HCID 688855731,1-Dimethylethyl 4-{[1-(cyclopropylmethyl)-4-piperidinyl]methyl}-1-piperidinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1,1-Dimethylethyl 4-(4-piperidinylmethyl)-1-piperidinecarboxylate (may be prepared as described in Description 2) (2.0 g), cyclopropyl carboxaldehyde (1.6 ml) and triethylamine (1.99 ml) were stirred in dichloromethane (70 ml) at room temperature. After 10 min sodium triacetoxyborohydride (3.1 g) was added and the reaction was stirred at room temperature overnight. The reaction mixture was washed with saturated potassium carbonate solution (2×50 ml), saturated sodium hydrogen carbonate solution (2×50 ml) and saturated brine (50 ml). The organic phase was dried (MgSO4) and evaporated to give the title compound (D9) (2.0 g).

Aufarbeitung

  1. washThe reaction mixture was washed with saturated potassium carbonate solution (2×50 ml), saturated sodium hydrogen carbonate solution (2×50 ml) and saturated brine (50 ml)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-591176b5fb1349b58f029f4d5b668bc4
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638631B2

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