3-(3-((7-chloro-2-quinolinyl)methoxy)phenyl)-4,5-dihydro-2-benzoxepin-1(3H)-one → 1-(2-(3-(3-((7-Chloro-2-quinolinyl)methoxy)phenyl)-3-hydroxypropyl)phenyl)cyclopentanol

HRID 258478Notes

Reaction equation

HRID 258478 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH:20]4[CH2:26][CH2:25][C:24]5[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=5[C:22](=[O:31])[O:21]4)[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.Br[Mg][CH2:34][CH2:35][CH2:36][CH2:37][Mg]Br>C1COCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH:20]([OH:21])[CH2:26][CH2:25][C:24]4[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=4[C:22]4([OH:31])[CH2:37][CH2:36][CH2:35][CH2:34]4)[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 197372293-(3-((7-chloro-2-quinolinyl)methoxy)phenyl)-4,5-dihydro-2-benzoxepin-1(3H)-oneHCID 178419681HCID 178419681, compound

Product 1

HCID 197372621-(2-(3-(3-((7-Chloro-2-quinolinyl)methoxy)phenyl)-3-hydroxypropyl)phenyl)cyclopentanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the lactone of Step 4 (1.004 g, 2.335 mmol) in 5 mL of anhydrous THF at r.t., a suspension of 0.70M 1,4-di(bromomagnesio)butane in THF (J. Org. Chem., 45, 1828 (1980); 5.3 mL, 3.7 mmol) was added dropwise and the mixture was stirred for 30 min and was quenched at 0° C. with cold 25% aq NH4OAc. The title cyclopentanol was extracted with EtOAc, dried over Na2SO4 and purified by flash chromatography on silica using EtOAc:toluene 15:85 and 20:80. Yield: 1.006 g, 88%.

Workup

  1. additionwas added dropwise
  2. customwas quenched at 0° C. with cold 25% aq NH4OAc
  3. extractionThe title cyclopentanol was extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. custompurified by flash chromatography on silica

Sources & evidence

ORD record
ord-1ae7d1c9e8884debacccef727921e97b
Source dataset
uspto-grants-1993_11
Patent number
US05266568

Reaction notes

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