Boron Trichloride → {4-[(7-Hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-piperidin-1-yl}-morpholin-4-yl-methanone

HRID 988297ノート

反応式

HRID 988297 の反応式
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([N:13]([CH2:28][CH2:29][CH3:30])[CH:14]3[CH2:19][CH2:18][N:17]([C:20]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[O:21])[CH2:16][CH2:15]3)[CH2:10]2)=[CH:5][CH:4]=1.B(Cl)(Cl)Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([N:13]([CH2:28][CH2:29][CH3:30])[CH:14]3[CH2:15][CH2:16][N:17]([C:20]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[O:21])[CH2:18][CH2:19]3)[CH2:10]2)=[CH:5][CH:4]=1

参加物

5

反応物 2

HCID 25135Boron TrichlorideHCID 10216398HCID 10216398、化合物

生成物 1

HCID 22649552{4-[(7-Hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-piperidin-1-yl}-morpholin-4-yl-methanone収率 44.3%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6344Dichloromethane溶媒

実験手順

To a −78° C. solution of {4-[(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-piperidin-1-yl}-morpholin-4-yl-methanone (300 mg, 0.72 mmol) and tetrabutylammonium iodide (292 mg, 0.79 mmol) in dichloromethane (20 mL) under an inert atmosphere was added boron trichloride (1M, 2.5 mL, 2.5 mmol) dropwise. The reaction was warmed to room temperature and stirred for 2.5 h. The reaction was quenched by slow addition of water and the organic layer separated and dried (MgSO4). This was concentrated onto silica (1.5 g) and placed on top of a flash column. Chromatography eluting with 30% acetone in hexanes afforded {4-[(7-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-piperidin-1-yl}-morpholin-4-yl-methanone (128 mg).

後処理

  1. customThe reaction was quenched by slow addition of water
  2. customthe organic layer separated
  3. dry with materialdried (MgSO4)
  4. concentrationThis was concentrated onto silica (1.5 g)
  5. washChromatography eluting with 30% acetone in hexanes

出典と根拠

ORDレコード
ord-8485d4d382c740f4a0944bdc89b75d76
出典データセット
uspto-grants-2003_10
特許番号
US06635658B2

反応ノート

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