Triphenylcarbinol → HCID 9826097, compound

HRID 1955429Notes

Reaction equation

HRID 1955429 reaction equation
[CH2:1]([C@H:8]1[C:12](=[O:13])[O:11][C@@H:10]([CH2:14][S:15]C(=O)C)[CH2:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[BH4-].[Na+].[C:21](O)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CO>[CH2:1]([C@@H:8]1[CH2:9][C@H:10]([CH2:14][S:15][C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:11][C:12]1=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 6457TriphenylcarbinolHCID 4311764Sodium borohydrideHCID 11254299HCID 11254299, compound

Product 1

HCID 9826097HCID 9826097, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product of Example 13 in 100 mL of methanol, cooled to 0° C., was added 2.69 g (0.071 mol) of solid sodium borohydride in portions over 15 minutes. The reaction was then concentrated in vacuo, acidified with 10% HCl solution and extracted with methylene chloride. The combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting crude thiol was dissolved in 50 mL of trifluoroacetic acid and 5.98 g (0.023 mol) of trityl alcohol was added. After stirring at room temperature for 1 h the reaction mixture was concentrated in vacuo and the residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:50) to provide 5.26 g (61%) of the desired product as a colorless oil. CI Mass Spec: 473.5 (M+H).

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. extractionextracted with methylene chloride
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe resulting crude thiol was dissolved in 50 mL of trifluoroacetic acid
  8. concentrationwas concentrated in vacuo
  9. customthe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:50)

Sources & evidence

ORD record
ord-e14ae7a92b164cc39f5cd28a2c324667
Source dataset
uspto-grants-2000_09
Patent number
US06124502

Reaction notes

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