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Tributylphosphine → {(S)-6-[(R)-4-bromo-7-fluoro-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

HRID 237436
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HRID 237436 반응식
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[OH:17][C:18]1[CH:31]=[CH:30][C:21]2[C@H:22]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:23][O:24][C:20]=2[CH:19]=1.[Br:32][C:33]1[CH:41]=[CH:40][C:39]([F:42])=[C:38]2[C:34]=1[CH2:35][CH2:36][C@@H:37]2O.C(P(CCCC)CCCC)CCC>O1CCCC1>[Br:32][C:33]1[CH:41]=[CH:40][C:39]([F:42])=[C:38]2[C:34]=1[CH2:35][CH2:36][C@H:37]2[O:17][C:18]1[CH:31]=[CH:30][C:21]2[C@H:22]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:23][O:24][C:20]=2[CH:19]=1
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참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 53393313(S)-Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetateHCID 86697104(S)-4-bromo-7-fluoro-2,3-dihydro-1H-inden-1-ol

생성물 1

HCID 86697103{(S)-6-[(R)-4-bromo-7-fluoro-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of di-tert.-butyl azodicarboxylate (18 g) in tetrahydrofuran (80 mL) is added dropwise over 45 minutes to a solution of (S)-methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetate (11 g), (S)-4-bromo-7-fluoro-2,3-dihydro-1H-inden-1-ol (11.95 g) and tributylphosphine (19.3 mL) in tetrahydrofuran (320 mL) at −10° C. The resulting solution is stirred for 30 minutes and then partitioned between saturated aqueous NaHCO3 solution and dichloromethane. The aqueous phase is extracted with dichloromethane. The combined organic phases are dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→70:30) to give the title compound. Yield: 10.35 g; LC (method 1): tR=1.41 min; Mass spectrum (ESI+): m/z=421 [M+H]+.

후처리

  1. custompartitioned between saturated aqueous NaHCO3 solution and dichloromethane
  2. extractionThe aqueous phase is extracted with dichloromethane
  3. dry with materialThe combined organic phases are dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→70:30)

출처 및 근거

ORD 기록
ord-5f14dd3290f6417f989c945967d76d9e
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08642585B2

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