Sodium Hydroxide → tert-Butyl 4-(hydroxymethyl)-4-(pyridin-4-yl)piperidine-1-carboxylate

HRID 391458ノート

反応式

HRID 391458 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2([C:20](OCC)=[O:21])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C(#N)C.C(=O)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.C(OCC)(=O)C.O>[OH:21][CH2:20][C:7]1([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[CH2:11][CH2:12]1

参加物

9

反応物 5

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 589936931-tert-Butyl 4-ethyl 4-(pyridin-4-yl)piperidine-1,4-dicarboxylateHCID 86587134Acetonitrile dry ice

生成物 1

HCID 58993619tert-Butyl 4-(hydroxymethyl)-4-(pyridin-4-yl)piperidine-1-carboxylate収率 41.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A flask was charged with 1-tert-butyl 4-ethyl 4-(pyridin-4-yl)piperidine-1,4-dicarboxylate (250 mg, 0.748 mmol) in tetrahydrofuran (3 mL) and cooled to −50° C. (acetonitrile/dry ice). Lithium aluminum hydride (0.785 ml, 1.570 mmol) was added dropwise, and the reaction was allowed to stir for 30 min. The flask was then warmed to room temperature and slowly diluted with ethyl acetate (5 mL). Water (61 μL) was added and the reaction allowed to stir for 5 min. Sodium Hydroxide (1 N in water, 120 μL) was then added and the reaction allowed to stir for 5 min. An additional portion of water (61 μL) and a small amount of sodium sulfate was added and the resulting mixture allowed to stir for 5 min. The suspension was filtered through celite, and the resulting pad washed with hot ethyl acetate. The filtrate was concentrated in vacuo to yield 90 mg (41%) of desired product. Mass Spec.: 294.05 (MH)+. LC tr=1.79 min (HPLC Method 1).

後処理

  1. stirringto stir for 5 min
  2. stirringto stir for 5 min
  3. stirringto stir for 5 min
  4. filtrationThe suspension was filtered through celite
  5. washthe resulting pad washed with hot ethyl acetate
  6. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-83e02f72e1c848f9930a7c27687a9ab5
出典データセット
uspto-grants-2013_02
特許番号
US08383821B2

反応ノート

読み込み中…