Acetaldehyde → 4-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-ethyl-amino}-piperidine-1-carboxylic acid tert-butyl ester

HRID 14862

Reaktionsgleichung

Reaktionsgleichung von HRID 14862
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=O)[CH:5]=[CH:4][N:3]=1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].[CH:30](=O)[CH3:31].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([N:29]([CH2:11][C:10]2[CH:13]=[CH:14][CH:15]=[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH:9]=2)[CH2:30][CH3:31])[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Komponenten

5

Edukt 4

HCID 177AcetaldehydeHCID 12682914-Amino-1-Boc-piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 249019653-(2-Chloro-pyrimidin-4-yl)-benzaldehyde

Produkt 1

HCID 866032904-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-ethyl-amino}-piperidine-1-carboxylic acid tert-butyl ester

Versuchsvorschrift

Intermediate 1 was coupled with 4-Amino-piperidine-1-carboxylic acid tert-butyl ester following procedure B. When the starting aldehyde had been consumed, 2 equivalents each of acetaldehyde and sodium triacetoxyborohydride were added and the mixture stirred for another two hours. The organic layer was washed with water followed by sat. NaCl. The solvent was removed to give product LC-MS showed the product was >90% pure and had the expected M+H+ of 403, and it was used in the following reactions without purification.

Aufarbeitung

  1. customWhen the starting aldehyde had been consumed
  2. washThe organic layer was washed with water
  3. customThe solvent was removed
  4. customto give product LC-MS
  5. customwas used in the following reactions without purification

Quellen und Nachweise

ORD-Eintrag
ord-0997701628974c5a9df0267362e8f45d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732444B2

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