Diisopropylethylamine → (1R)-1'-({1-[4-(Pyridin-4-ylmethoxy)phenyl]cyclopropyl}-carbonyl)-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one

HRID 504294노트

반응식

HRID 504294 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH:14]1[CH2:18][CH2:17][C@@:16]2([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[C:20](=[O:27])[O:19]2)[CH2:15]1.[CH3:28][C:29]1(C)[C@@H]2CC[C@@:30]1([CH2:37]S(O)(=O)=O)[C:31](=O)[CH2:32]2.F[P-](F)(F)(F)(F)F.[N:50]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[N:50]1[CH:32]=[CH:31][C:30]([CH2:37][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3([C:11]([N:14]4[CH2:18][CH2:17][C@@:16]5([C:22]6[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=6[C:20](=[O:27])[O:19]5)[CH2:15]4)=[O:13])[CH2:9][CH2:10]3)=[CH:6][CH:7]=2)=[CH:29][CH:28]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 225049291-(4-Hydroxyphenyl)cyclopropane-1-carboxylic acidHCID 86602274[(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid (1R)-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one

생성물 1

HCID 66661855(1R)-1'-({1-[4-(Pyridin-4-ylmethoxy)phenyl]cyclopropyl}-carbonyl)-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one수율 89%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 1-(4-hydroxyphenyl)cyclopropanecarboxylic acid (0.20 g, 1.1 mmol), [(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid-(1R)-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one salt (0.47 g, 1.1 mmol), Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.55 g, 1.2 mmol), and N,N-diisopropylethylamine (0.49 ml, 2.8 mmol) in methylene chloride (3 ml) was stirred at r.t. overnight. Then the reaction was quenched with water, and the reaction mixture was extracted with ethyl acetate. The extract was washed with 1N HCl aqueous solution (×2), water and brine successively; then dried over Na2SO4; and then filtered. The filtrate was concentrated to afford the desired product (0.35 g, yield: 89%).

후처리

  1. customThen the reaction was quenched with water
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with 1N HCl aqueous solution (×2), water and brine successively
  4. dry with materialthen dried over Na2SO4
  5. filtrationand then filtered
  6. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-d0ec33ef2cbc4efaae4b1820c8cee636
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776874B2

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