Hydrochloric Acid → (R)-ethyl-3-(4-chlorophenyl)-hexahydro-1-pyrazinecarboxylate

HRID 2390923ノート

反応式

HRID 2390923 の反応式
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9](CC=C)[C@H:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:7]1)=[O:5])[CH3:2].O.Cl.[OH-].[Na+]>[Ru](Cl)(Cl)Cl.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][NH:9][C@H:8]([C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH2:7]1)=[O:5])[CH3:2]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68576864(R)-ethyl-3-(4-chlorophenyl)-4-(2-propenyl)hexahydro-1-pyrazinecarboxylate

生成物 1

HCID 68579181(R)-ethyl-3-(4-chlorophenyl)-hexahydro-1-pyrazinecarboxylate収率 38.8%

試薬・触媒・溶媒 2

HCID 61850Ruthenium trichloride触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To (R)-ethyl-3-(4-chlorophenyl)-4-(2-propenyl)hexahydro-1-pyrazinecarboxylate (212 mg, 0.69 mmol) produced in Example 24, distilled water (2 mL), conc. hydrochloric acid (71 mg, 1.0 equivalent) and ruthenium chloride (7 mg, 0.04 equivalent) were added. The mixture was stirred at 100° C. for 93 hours. After toluene (2 mL) was added thereto, the formed insolubles were separated by filtration and washed with toluene (2 mL) and distilled water (2 mL). To the filtrate, 30 wt % aqueous solution sodium hydroxide (110 mg, 1.2 equivalents) was added. The organic layer and aqueous layer were separated, and the organic layer was washed twice with distilled water (4 mL). The obtained organic layer was concentrated and dried under vacuum, to obtain 72 mg of the title compound as pale brown oil (yield: 38%, chemical purity: 92.6 area %). The retention time in the chemical purity analysis method was 2.9 min.

後処理

  1. additionwere added
  2. customthe formed insolubles were separated by filtration
  3. washwashed with toluene (2 mL)
  4. distillationdistilled water (2 mL)
  5. customThe organic layer and aqueous layer were separated
  6. washthe organic layer was washed twice with distilled water (4 mL)
  7. concentrationThe obtained organic layer was concentrated
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-8e7a6a6f0f2f4d91af0aa6c0b6df5c7c
出典データセット
uspto-grants-2012_09
特許番号
US08273883B2

反応ノート

読み込み中…