Sodium Iodide → benzyl (2R)-2-benzyl-5-morpholin-4-yl-4-oxopentanoate

HRID 973505ノート

反応式

HRID 973505 の反応式
[CH2:1]([C@H:8]([CH2:19][C:20]([CH2:22]Cl)=[O:21])[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[I-].[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([C@H:8]([CH2:19][C:20](=[O:21])[CH2:22][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 5238Sodium IodideHCID 8083MorpholineHCID 10449338Benzyl (2R)-2-Benzyl-3-chloromethylcarbonylpropionate

生成物 1

HCID 10452445benzyl (2R)-2-benzyl-5-morpholin-4-yl-4-oxopentanoate収率 65.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

The resultant compound from Example 34 (610 mg, 1.84 mmol) in dimethylformamide (10 ml) was treated with NaI (33 mg, 0.22 mmol) and morpholine (0.60 ml, 6.88 mmol). After 2 h the mixture was diluted with ethyl acetate, washed with water and brine, and then dried over Na2SO4, and evaporated. Chromatography of the residue on silica gel with 60% ethyl acetate/40% hexane afforded 460 mg (65%) of an oil. 1H NMR (CDCl3) δ7.05-7.40 (m,10H), 5.11 (d,1H), 5.06 (d,1H), 3.68 (m,4H), 3.22-3.32 m,1H), 3.15 (d,1H), 3.08 (d,1H), 3.05 (m,1H), 2.87 (dd,1H), 2.77 (dd,1H), 2.35-2.50 (m,5H).

後処理

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. customevaporated

出典と根拠

ORDレコード
ord-ac3cdb5e919f4e49884ec53454de2383
出典データセット
uspto-grants-1991_11
特許番号
US05063208

反応ノート

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