Sodium borohydride → HCID 17866627, compound

HRID 583372Notes

Reaction equation

HRID 583372 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[C:8]([CH:10]=[O:11])[CH:7]=[C:6]([CH3:12])[C:5]=1[N:13]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)(=[O:16])=[O:15].[BH4-].[Na+]>CO.C1COCC1>[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[C:6]([CH3:12])[C:5]=1[N:13]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)(=[O:15])=[O:16]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86754312HCID 86754312, compound

Product 1

HCID 17866627HCID 17866627, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a mixture of 907 mg (2.0 mmol) of the product of Example 268 in 50 ml of MeOH:THF (4:1) was added sodium borohydride. The reaction was then stilred at room temperature for 30 min and concentrated in vacuo. The residue was dissolved in dichloromethane, washed with 5% HCl and brine, dried over MgSO4, filtered and concentrated in vacuo to provide 872 mg (96%) of the desired product as a white crystalline solid. Electrospray Mass Spec 456 (M+H).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with 5% HCl and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb7efc484297485a89b1fce5cb0d610e
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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