Tetrahydrofuran → morpholine 5-(2-Benzyloxyphenyl)-3-oxo-pent-4-ynamide

HRID 1463925

反応式

HRID 1463925 の反応式
[C:1]([N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].C(O[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:24]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=O)C#C.[O:38]1CC[CH2:40][CH2:39]1>O>[NH:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[CH2:31]([O:30][C:24]1[CH:23]=[CH:28][CH:27]=[CH:26][C:25]=1[C:29]#[C:40][C:39](=[O:38])[CH2:2][C:1]([NH2:4])=[O:3])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

参加物

6

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 155434-AcetylmorpholineHCID 2724682Lithium diisopropylamideHCID 54058410Methyl-2-benzyloxyphenyl propiolate

生成物 1

HCID 86747286morpholine 5-(2-Benzyloxyphenyl)-3-oxo-pent-4-ynamide収率 61%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

Acetyl morpholine (546 ul, 4.72 mmole) was dissolved in 10 ml dry tetrahydrofuran in an oven dried 50 ml two neck round bottom flask under nitrogen. The solution was cooled to 0° C. and was treated slowly dropwise with lithium diisopropylamide (3.2 ml, 4.72 mmole). The mixture was stirred 30 minutes at 0° C. and was treated with methyl-2-benzyloxyphenyl propiolate (600 mg, 2.25 mmole) in 2 ml dry tetrahydrofuran. The reaction mixture was stirred for 1 hour at 0° C. and was diluted with 10 ml water. The volatiles were removed in vacuo and the residue was crystallized from diethyl ether/methanol (20:1). The tan solid was collected, was washed with diethyl ether, and was dried to afford 500 mg (61%) of morpholine-5-(2-Benzyloxyphenyl)-3-oxo-pent-4-ynamide as a tan solid. Melting Point: 224°-227° C.

後処理

  1. dry with materialdried 50 ml two neck round bottom flask under nitrogen
  2. stirringThe reaction mixture was stirred for 1 hour at 0° C.
  3. customThe volatiles were removed in vacuo
  4. customthe residue was crystallized from diethyl ether/methanol (20:1)
  5. customThe tan solid was collected
  6. washwas washed with diethyl ether
  7. customwas dried

出典と根拠

ORDレコード
ord-c351075d065040a1ba1d312e4d965ae0
出典データセット
uspto-grants-1994_04
特許番号
US05302613

関連ノート

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