Ethyl 2-formylcyclopropanecarboxylate → HCID 178468463、化合物

HRID 555265

反応式

HRID 555265 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([N:11]2[CH2:17][C:16]3([CH3:19])[CH2:18][CH:12]2[CH2:13][C:14]([CH3:21])([CH3:20])[CH2:15]3)=[O:10])[CH:5]=[CH:6][C:7]=1[NH2:8].[CH:22]([CH:24]1[CH2:26][CH:25]1[C:27]([O:29][CH2:30][CH3:31])=[O:28])=O>CN1C(=O)CCC1>[CH2:30]([O:29][C:27]([CH:25]1[CH2:26][CH:24]1[C:22]1[NH:8][C:7]2[CH:6]=[CH:5][C:4]([C:9]([N:11]3[CH2:17][C:16]4([CH3:19])[CH2:18][CH:12]3[CH2:13][C:14]([CH3:21])([CH3:20])[CH2:15]4)=[O:10])=[CH:3][C:2]=2[N:1]=1)=[O:28])[CH3:31]

参加物

4

反応物 2

HCID 89334Ethyl 2-formylcyclopropanecarboxylateHCID 66987132HCID 66987132、化合物

生成物 1

HCID 178468463HCID 178468463、化合物収率 8.4%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
50 °C

実験手順

To a solution of (3,4-diaminophenyl)-(1,3,3-trimethyl-6-azabicyclo[3.2.1]oct-6-yl)methanone (500 mg, 1.74 mmol) in dry NMP (25 mL) at room temperature under an inert atmosphere of nitrogen was added approx. 500 mg of molecular sieve 4 Å followed by ethyl 2-formyl-1-cyclopropanecarboxylate (0.51 mL, 3.86 mmol). The mixture was stirred for 16 hrs at 50° C. The reaction was quenched by the addition of water (100 mL) followed by extraction with diethyl ether (3×100 mL). The combined organic phases were washed with water (3×100 mL), brine (100 mL), dried (MgSO4), filtered, and evaporated in vacuo. The resulting oil was purified by preparative HPLC, dried in vacuo at 50° C. affording 60 mg (8%) of the title compound as a solid. MS-ESI m/z 410; 1H NMR (400 MHz, CDCl3) δ 0.88-1.06 (m, 6H), 1.07-1.20 (m, 4H), 1.25 (t, 3H), 1.27-1.34 (m) and 1.49-1.66 (m, 3H), 1.36-1.48 (m, 2H), 1.72-1.84 (m, 2H), 2.36-2.48 (m, 1H), 2.66-2.76 (m, 1H), 3.18-3.27 (m, 1H), 3.30 (d) and 3.65 (d, 1H), 4.00-4.06 (m) and 4.57-4.65 (m, 1H), 4.14 (q, 2H), 7.18-7.30 (m, 2H), 7.57 (d, 1H), 10.37 (br s, 1H).

後処理

  1. customThe reaction was quenched by the addition of water (100 mL)
  2. extractionfollowed by extraction with diethyl ether (3×100 mL)
  3. washThe combined organic phases were washed with water (3×100 mL), brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe resulting oil was purified by preparative HPLC
  8. customdried in vacuo at 50° C.

出典と根拠

ORDレコード
ord-3a8684624e734afa91e55e88544b4a25
出典データセット
uspto-grants-2011_11
特許番号
US08053431B2

関連ノート

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