Cyclohexanone → N-(1-Cyclohexyl-piperidin-4-yl)-N-(4-fluoro-phenyl)-acetamide

HRID 507859ノート

反応式

HRID 507859 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[C:18]1(=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH:18]1([N:15]2[CH2:16][CH2:17][CH:12]([N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:9](=[O:11])[CH3:10])[CH2:13][CH2:14]2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

参加物

5

反応物 3

HCID 7967CyclohexanoneHCID 5049666Sodium triacetoxyborohydrideHCID 18539208HCID 18539208、化合物

生成物 1

HCID 11951208N-(1-Cyclohexyl-piperidin-4-yl)-N-(4-fluoro-phenyl)-acetamide

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

N-(4-fluoro-phenyl)-N-piperidin-4-yl-acetamide (60 mg; 0.25 mmol; 1 eq.), see Example 6 for deprotection procedure, and cyclohexanone (29 mg; 0.30 mmol; 1.2 eq.) were dissolved in DCE (2 mL). NaBH(OAc)3 (108 mg; 0.51 mmol; 2 eq.) was added, and the reaction was stirred at room temperature for 72 hours and then quenched with 1N NaOH (5 mL). DCM (5 mL) was then added and the layers were separated. The aqueous layer was washed with DCM (10 mL) and the combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified using reversed-phase HPLC (2-99% CH3CN/H2O gradient with 0.05% TFA). LC/MS M/Z 319.2, Retention time=1.88 minutes; 10-99% CH3CN/H2O gradient with 0.05% TFA.

後処理

  1. customquenched with 1N NaOH (5 mL)
  2. additionDCM (5 mL) was then added
  3. customthe layers were separated
  4. washThe aqueous layer was washed with DCM (10 mL)
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude residue was purified

出典と根拠

ORDレコード
ord-bb8fe3bf796a4fbd91d29254726acbee
出典データセット
uspto-grants-2010_08
特許番号
US07786308B2

反応ノート

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