Acetic Acid → HCID 57494025、化合物

HRID 888945ノート

反応式

HRID 888945 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][CH2:16][O:17][CH3:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:19]1[CH:23]=[CH:22][N:21]=[C:20]1[CH:24]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([CH2:15][CH2:16][O:17][CH3:18])[CH2:24][C:20]2[S:19][CH:23]=[CH:22][N:21]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 27349031,3-Thiazole-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 43652134tert-Butyl 4-[(2-methoxyethyl)amino]piperidine-1-carboxylate

生成物 1

HCID 57494025HCID 57494025、化合物

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 4-(2-methoxy-ethylamino)-piperidine-1-carboxylic acid tert-butyl ester (465 mg), and 2-thiazolecarboxaldehyde (190 μl) stirring in anhydrous 1,2-dichloroethane (5 ml) was added glacial acetic acid (1 equiv.) and sodium triacetoxyborohydride (458 mg). The reaction mixture was stirred for 12 hours at room temperature, then diluted with dichloromethane (40 ml), washed with brine, dried (MgSO4) and the solvents removed in vacuo. The residue was purified using flash silica chromatography to give 4[(2-methoxy-ethyl)-thiazol-2-ylmethyl-amino]-piperidine-1-carboxylic acid tert-butyl ester (574 mg). Treatment of this compound with HCl in dichloromethane/methanol and a basic wash with sodium hydrogen carbonate yielded (2-methoxy-ethyl)-piperidin-4-yl-thiazol-2-ylmethyl-amine.

後処理

  1. washwashed with brine
  2. dry with materialdried (MgSO4)
  3. customthe solvents removed in vacuo
  4. customThe residue was purified

出典と根拠

ORDレコード
ord-91b81e0e2d4f4ab0a90905960dd6df27
出典データセット
uspto-grants-2012_08
特許番号
US08252792B2

反応ノート

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