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Tributylphosphine → {(S)-6-[(R)-4-bromo-5-cyano-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

HRID 2406506
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HRID 2406506 반응식
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[CH3:17][O:18][C:19](=[O:31])[CH2:20][C@H:21]1[C:25]2[CH:26]=[CH:27][C:28]([OH:30])=[CH:29][C:24]=2[O:23][CH2:22]1.[Br:32][C:33]1[C:41]([C:42]#[N:43])=[CH:40][CH:39]=[C:38]2[C:34]=1[CH2:35][CH2:36][C@@H:37]2O.C(P(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH3:17][O:18][C:19](=[O:31])[CH2:20][C@H:21]1[C:25]2[CH:26]=[CH:27][C:28]([O:30][C@H:37]3[C:38]4[C:34](=[C:33]([Br:32])[C:41]([C:42]#[N:43])=[CH:40][CH:39]=4)[CH2:35][CH2:36]3)=[CH:29][C:24]=2[O:23][CH2:22]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 13831TributylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 53393313(S)-Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetateHCID 86700772(S)-4-bromo-1-hydroxy-indan-5-carbonitrile

생성물 1

HCID 86700771{(S)-6-[(R)-4-bromo-5-cyano-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회
HCID 8857Ethyl Acetate용매

실험 절차

A solution of di-tert-butyl azodicarboxylate (3.30 g) in tetrahydrofuran (5 mL) is added dropwise over 45 min to a solution of (S)-(6-hydroxy-2,3-dihydro-benzofuran-3-yl)-acetic acid methyl ester (for preparation see WO 2008001931; 2.10 g), (S)-4-bromo-1-hydroxy-indan-5-carbonitrile (2.40 g) and tri-n-butyl-phosphine (3.8 mL) in tetrahydrofuran (25 mL) at −10° C. The resulting solution is stirred for 30 min and then diluted with ethyl acetate. The resulting solution is washed with water and brine and dried (MgSO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30) to give the title compound. LC (method 2): tR=1.15 min; Mass spectrum (ESI+): m/z=428/430 (Br) [M+H]+.

후처리

  1. washThe resulting solution is washed with water and brine
  2. dry with materialdried (MgSO4)
  3. customThe solvent is evaporated
  4. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30)

출처 및 근거

ORD 기록
ord-c93fc37960634a7d8e68ee58b7544272
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08809376B2

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