Tetrahydrofuran → HCID 58869125, compound

HRID 2355230Notes

Reaction equation

HRID 2355230 reaction equation
C[O:2][C:3](=O)[CH2:4][NH:5][CH2:6][C@H:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][C:11]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])=[CH:12][CH:13]=2)[O:8]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:33]1COCC1>>[C:20]1([S:17]([C:11]2[CH:10]=[C:9]3[C:14]([CH2:15][CH2:16][C@H:7]([CH2:6][N:5]([CH3:33])[CH2:4][CH2:3][OH:2])[O:8]3)=[CH:13][CH:12]=2)(=[O:18])=[O:19])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 58869158HCID 58869158, compound

Product 1

HCID 58869125HCID 58869125, compound

Procedure

(R)-[(7-benzenesulfonyl-chroman-2-ylmethyl)-amino]-acetic acid methyl ester (40 mg, 1 mmol) was dissolved in 2 mL dry THF under Ar atmosphere. LAH (0.25 mL of 1M solution in THF) was added dropwise, and the reaction mixture was stirred for one hour. The reaction was quenched by addition of aqueous sodium sulfate solution. The mixture was extracted with methylene chloride and the combined organic layers were washed with water and brine, dried (Na2SO4), filtered and contrated under reduced pressure. The residue was recrystallized from diethyl ether and 1 M HCl in EtOH to give 32.2 mg of (R)-2-[(7-Benzenesulfonyl-chroman-2-ylmethyl)-methyl-amino]-ethanol as a hydrochloride, MS (M+H)=362.

Workup

  1. customThe reaction was quenched by addition of aqueous sodium sulfate solution
  2. extractionThe mixture was extracted with methylene chloride
  3. washthe combined organic layers were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe residue was recrystallized from diethyl ether and 1 M HCl in EtOH

Sources & evidence

ORD record
ord-a236dc0b99f44107bbf0fbfe75dfe56d
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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