D-1,4-Dithiothreitol → (7-Mercapto-indan-4-yloxy)-acetic Acid Methyl Ester

HRID 1296036Notes

Reaction equation

HRID 1296036 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:12]([S:15]C#N)=[C:11]2[C:7]=1[CH2:8][CH2:9][CH2:10]2.SC[C@H]([C@@H](CS)O)O.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:18])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:12]([SH:15])=[C:11]2[C:7]=1[CH2:8][CH2:9][CH2:10]2

Participants

5

Reactant 3

HCID 446094D-1,4-DithiothreitolHCID 4311764Sodium borohydrideHCID 20770873(7-Thiocyanato-indan-4-yloxy)-acetic acid methyl ester

Product 1

HCID 20770872(7-Mercapto-indan-4-yloxy)-acetic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(7-Thiocyanato-indan-4-yloxy)-acetic acid methyl ester (Example 1C) (3.09 g, 12.9 mmol) was dissolved in 30 ml methanol. Dithiothreitol (2.6 g) was added followed by sodium borohydride (200 mg). The reaction was stirred for 1 hour followed by concentration to an oil. The crude product was dissolved in 200 ml dichloromethane and filtered through silica gel and eluted with 200 ml dichloromethane. The product was then recrystallized from ethyl acetate/heaxanes to afford the title product. MS m/z 239 (M+1).

Workup

  1. concentrationfollowed by concentration to an oil
  2. dissolutionThe crude product was dissolved in 200 ml dichloromethane
  3. filtrationfiltered through silica gel
  4. washeluted with 200 ml dichloromethane
  5. customThe product was then recrystallized from ethyl acetate/heaxanes

Sources & evidence

ORD record
ord-5ee3a684125441ac8162075cf56da532
Source dataset
uspto-grants-2007_07
Patent number
US07244763B2

Reaction notes

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