Phthalimide → Triphenylphosphine Oxide

HRID 60785

반응식

HRID 60785 반응식
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([N:9]1[CH2:13][C@H:12]([OH:14])[CH2:11][C@H:10]1[CH2:15]O)=[O:8].[C:23]1(=[O:33])[NH:27][C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12.[C:34]1([P:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=[O:56]>C1COCC1>[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:2]([C:7]([N:9]2[CH2:13][C@H:12]([OH:14])[CH2:11][C@H:10]2[CH2:15][N:27]2[C:23](=[O:33])[C:24]3[C:25](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:26]2=[O:28])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:47]1([P:40](=[O:56])([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

참가 물질

7

반응물 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 89739118biphenyl-2-yl((2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidin-1-yl)methanone

생성물 2

HCID 13097Triphenylphosphine OxideHCID 897481992-(((2S,4R)-1-(biphenylcarbonyl)-4-hydroxypyrrolidin-2-yl)methyl)isoindoline-1,3-dione

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of biphenyl-2-yl((2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidin-1-yl)methanone (1.67 g, 5.6 mmol), phthalimide (1.24 g, 8.4 mmol) and triphenylphosphine (2.20 g, 8.4 mmol) in THF (56 mL) was cooled to 0° C. and added with diisopropyl azodicarboxylate (DIAD; 1.63 mL, 8.4 mmol) dropwise. The resulting suspension was allowed to warm to rt gradually and stirred overnight, concentrated in vacuo to a brown oil which was eluted on silica gel column (70% EtOAc in Hexanes) to provide 2-(((2S,4R)-1-(biphenylcarbonyl)-4-hydroxypyrrolidin-2-yl)methyl)isoindoline-1,3-dione as a white solid contaminated with triphenylphosphine oxide and used as-is.

후처리

  1. concentrationconcentrated in vacuo to a brown oil which
  2. washwas eluted on silica gel column (70% EtOAc in Hexanes)

출처 및 근거

ORD 기록
ord-cf77ff791e66417280225ff443b2bcc8
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440982B2

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