Water → HCID 21706365, compound

HRID 1595052Notes

Reaction equation

HRID 1595052 reaction equation
C([O:3][C:4](=[O:40])[CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[S:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[C:17]=2[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][N:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)=[CH:28][CH:27]=2)=[CH:12][CH:11]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH2:47].C1C[O:51]CC1>O.[OH-].[Na+]>[C:4]([OH:3])(=[O:40])[C:5]([OH:51])=[O:47].[N:35]1([CH2:34][CH2:33][O:32][C:29]2[CH:28]=[CH:27][C:26]([CH2:25][C:17]3[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[S:20][C:16]=3[C:13]3[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][OH:3])=[CH:11][CH:12]=3)=[CH:31][CH:30]=2)[CH2:36][CH2:37][CH2:38][CH2:39]1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 20682330HCID 20682330, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21706365HCID 21706365, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalyst2×HCID 14798Sodium HydroxideCatalyst

Procedure

5-[4-[3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophen-2-yl]phenoxy]pentanoic acid ethyl ester prepared in part A (78 mg; 0.14 mmol) was dissolved in 3 mL of anhydrous THF under an argon atmosphere, then LAH (10 mg; 0.29 mmol) was added. The resultant mixture was stirred at room temperature for 3 h. To the reaction was added 1 drop of water, 1 drop of 5 M NaOH, and 3 drops of water. The mixture was stirred at room temperature for 45 min, then water (25 mL) was added. Extraction was carried out with EtOAc (4×25 mL). The combined organics were dried by passage through Na2SO4. The product was isolated as a colorless oil (49 mg; 66%) by flash chromatography on silica gel, eluting with EtOAc(10-90%)/Et3N(0-5%)/MeOH(0-5%). Conversion to the oxalate was effected in the usual way.

Workup

  1. extractionExtraction
  2. dry with materialThe combined organics were dried by passage through Na2SO4
  3. customThe product was isolated as a colorless oil (49 mg; 66%) by flash chromatography on silica gel
  4. washeluting with EtOAc(10-90%)/Et3N(0-5%)/MeOH(0-5%)

Sources & evidence

ORD record
ord-5fc15325881f4e458ab4b49227eff25f
Source dataset
uspto-grants-2001_09
Patent number
US06284756B1

Reaction notes

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