Triphenylphosphine → [4-(Pyrazin-2-ylmethoxy)-phenyl]-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

HRID 642205ノート

反応式

HRID 642205 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C@H:11]2[CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:9])=[CH:4][CH:3]=1.[N:21]1[CH:26]=[CH:25][N:24]=[CH:23][C:22]=1[CH2:27]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[N:21]1[CH:26]=[CH:25][N:24]=[CH:23][C:22]=1[CH2:27][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C@H:11]2[CH2:15][N:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)=[O:9])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 201734PyrazinemethanolHCID 5462977Diethyl azodicarboxylateHCID 11960316(4-hydroxy-phenyl)-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

生成物 1

HCID 11588685[4-(Pyrazin-2-ylmethoxy)-phenyl]-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone収率 1.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of (4-Hydroxy-phenyl)-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone (0.57 g, 2.0 mmol), pyrazin-2-yl-methanol [CAS 6705-33-5] (0.25 g, 2.3 mmol), and triphenylphosphine (0.57 g, 2.2 mmol) in THF (20 mL) is added DEAD (0.36 mL, 2.3 mmol). The mixture is stirred at room temperature overnight and partitioned between ethyl acetate and water. The aqueous phase is extracted with ethyl acetate (2×), and the combined organic phase is dried (Na2SO4) and concentrated. The crude material is purified by SCX chromatography followed by silica gel chromatography eluting with 20% (10% 2M MeOH/CH2Cl2)/80% CH2Cl2 to 70% (10% 2M MeOH/CH2Cl2)/30% CH2Cl2 to yield 12 mg of the title compound. MS (ES+) 367.3

後処理

  1. custompartitioned between ethyl acetate and water
  2. extractionThe aqueous phase is extracted with ethyl acetate (2×)
  3. dry with materialthe combined organic phase is dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude material is purified by SCX chromatography
  6. washeluting with 20% (10% 2M MeOH/CH2Cl2)/80% CH2Cl2 to 70% (10% 2M MeOH/CH2Cl2)/30% CH2Cl2

出典と根拠

ORDレコード
ord-1d00b1a2b22b4c7fa34035716e2cef49
出典データセット
uspto-grants-2010_04
特許番号
US07696234B2

反応ノート

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