Dichloromethane → Ammonia dichloromethane

HRID 33730

反応式

HRID 33730 の反応式
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19]1([C:25]2([OH:31])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].[CH2:48]([Cl:50])[Cl:49]>C(O)(=O)C>[NH3:1].[CH2:48]([Cl:50])[Cl:49].[C:19]1([C:25]2([OH:31])[CH2:30][CH2:29][N:28]([CH2:15][C:14]3[CH:17]=[CH:18][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:12][CH:13]=3)[CH2:27][CH2:26]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

参加物

8

反応物 5

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 963874-Phenylpiperidin-4-olHCID 27663244-(3-Piperidin-1-ylpropoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

生成物 2

HCID 102231854-Phenyl-1-[4-(3-piperidin-1-yl-propoxy)-benzyl]-piperidin-4-olHCID 22731429Ammonia dichloromethane収率 1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of the product of Example 9 (210 mg), 4-Phenyl-piperidin-4-ol (150 mg), and acetic acid (0.05 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (290 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (5 mL) and extracted with DCM (3×10 mL). The combined organic phases were dried (sodium sulfate) and evaporated. Chromatography of the residue (1-5% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (225 mg). 1H NMR (400 MHz, CDCl3): 7.54-7.49 (m, 2H), 7.37-7.33 (m, 2H), 7.28-7.23 (m, 3H), 6.88-6.84 (m, 2H), 3.99 (t, J=6.3 Hz, 2H), 3.51 (s, 2H), 2.78 (m, 2H), 2.50-2.36 (m, 8H), 2.15 (m, 2H), 1.97 (m, 2H), 1.73 (m, 2H), 1.63-1.55 (m, 4H), 1.47-1.40 (m, 2H).

後処理

  1. extractionextracted with DCM (3×10 mL)
  2. dry with materialThe combined organic phases were dried (sodium sulfate)
  3. customevaporated

出典と根拠

ORDレコード
ord-dbdea33fac0c4bb78f92332e09f2f2db
出典データセット
uspto-grants-2008_09
特許番号
US07429586B2

関連ノート

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