Triethylamine → [(S)-3-(4-Fluoro-benzyl)piperidin-1-yl]-[(3S,4R)-3-((R)-1-phenyl-ethylamino)-tetrahydro-pyran-4-yl]-methanone

HRID 497491ノート

反応式

HRID 497491 の反応式
[C:1]1([C@H:7]([NH:9][C@H:10]2[C@H:15]([C:16]([OH:18])=O)[CH2:14][CH2:13][O:12][CH2:11]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(N(CC)CC)C.[F:59][C:60]1[CH:72]=[CH:71][C:63]([CH2:64][C@@H:65]2[CH2:70][CH2:69][CH2:68][NH:67][CH2:66]2)=[CH:62][CH:61]=1>ClCCl>[F:59][C:60]1[CH:61]=[CH:62][C:63]([CH2:64][C@@H:65]2[CH2:70][CH2:69][CH2:68][N:67]([C:16]([C@@H:15]3[CH2:14][CH2:13][O:12][CH2:11][C@H:10]3[NH:9][C@@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH3:8])=[O:18])[CH2:66]2)=[CH:71][CH:72]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 12174831(S)-3-(4-Fluorobenzyl)piperidineHCID 59042160(3S,4R)-3-[(R)-1-Phenyl-ethylamino]-tetrahydro-pyran-4-carboxylic acid

生成物 1

HCID 69748122[(S)-3-(4-Fluoro-benzyl)piperidin-1-yl]-[(3S,4R)-3-((R)-1-phenyl-ethylamino)-tetrahydro-pyran-4-yl]-methanone収率 100%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A cloudy solution of (3S,4R)-3-[(R)-1-Phenyl-ethylamino]-tetrahydro-pyran-4-carboxylic acid (containing sodium chloride; 943 mg, 2.57 mmol) in dichloromethane (25 mL) was treated with benzotriazol-1-yloxy-tripyrrolidinophosphonium hexafluorophosphate (1.61 g, 3.09 mmol) and triethylamine (826 μL, 5.92 mmol) and stirred for 5 minutes. A solution of the (S)-3-(4-fluorobenzyl)-piperidine prepared above in dichloromethane (5 mL) was added and the mixture was stirred at room temperature. After 18 h, the mixture was washed with water and saturated NaHCO3, dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (75% ethyl acetate/hexanes) to provide the product as a gum (1.10 g, 100%).

後処理

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature
  3. waitAfter 18 h
  4. washthe mixture was washed with water and saturated NaHCO3
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (75% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-26d0ae3fda434d5db39e21706aad84e9
出典データセット
uspto-grants-2005_09
特許番号
US06949546B2

反応ノート

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