Sodium Hydroxide → (R)-3-(4-chlorophenyl)-1-(phenylmethyl)hexahydropyrazine dihydrochloride

HRID 2390919ノート

反応式

HRID 2390919 の反応式
[ClH:1].Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:15][N:14]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:12][N:11]2CC=C)=[CH:6][CH:5]=1.[OH-].[Na+]>[Ru](Cl)(Cl)Cl.C1(C)C=CC=CC=1>[ClH:3].[ClH:1].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C@H:10]2[NH:11][CH2:12][CH2:13][N:14]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:15]2)=[CH:8][CH:9]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 68577180(R)-2-(4-chlorophenyl)-4-(phenylmethyl)-1-(2-propenyl)hexahydropyrazine dihydrochloride

生成物 1

HCID 68578904(R)-3-(4-chlorophenyl)-1-(phenylmethyl)hexahydropyrazine dihydrochloride収率 87%

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

Mixed were (R)-2-(4-Chlorophenyl)-4-(phenylmethyl)-1-(2-propenyl)hexahydropyrazine dihydrochloride (104 mg, 0.25 mmol) produced in Example 18 and ruthenium chloride (3 mg, 0.04 mmol). The mixture was stirred at 100° C. for 24 hours. To the mixture, 30 wt % aqueous solution of sodium hydroxide (85 mg, 2.5 equivalents) and toluene (2 mL) were added. The formed insolubles were separated by filtration, and washed with distilled water (2 mL) and toluene (2 mL). After the organic layer and aqueous layer of the filtrate were separated, the organic layer was washed twice with distilled water (4 mL). The obtained organic layer was concentrated and dried under vacuum, to obtain 68 mg of the crude product of the title compound as pale brown oil (yield: 87%, chemical purity: 93.5 area %, optical purity: 98.1% e.e.). The retention time in the chemical purity analysis method was 3.1 min.

後処理

  1. additionMixed
  2. customThe formed insolubles were separated by filtration
  3. washwashed with distilled water (2 mL) and toluene (2 mL)
  4. customAfter the organic layer and aqueous layer of the filtrate were separated
  5. washthe organic layer was washed twice with distilled water (4 mL)
  6. concentrationThe obtained organic layer was concentrated
  7. customdried under vacuum

出典と根拠

ORDレコード
ord-6b48065f8e2b4c9cb5da246eaee62ab6
出典データセット
uspto-grants-2012_09
特許番号
US08273883B2

反応ノート

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