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

HRID 14862

反応式

HRID 14862 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0997701628974c5a9df0267362e8f45d
出典データセット
uspto-grants-2010_06
特許番号
US07732444B2

関連ノート

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