Sodium borohydride → HCID 86718360, compound

HRID 1518754Notes

Reaction equation

HRID 1518754 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:24])[C@H:9]([C:19]1[O:20][CH:21]=[CH:22][CH:23]=1)[C@H:10]([CH3:18])[CH2:11][O:12][CH2:13][C:14](OC)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[O:20]1[CH:21]=[CH:22][CH:23]=[C:19]1[C@@H:9]([N:8]([CH3:24])[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[C@H:10]([CH3:18])[CH2:11][O:12][CH2:13][CH2:14][OH:15]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86718361HCID 86718361, compound

Product 1

HCID 86718360HCID 86718360, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound 2.7a (0.95 g, 2.78 mmol) in methanol (7 mL) was added sodium borohydride (1.05 g, 27.8 mmol, 10.0 equiv) at 0° C. After stirring for 1 hour, the reaction was quenched with 1.0 M sulfuric acid and extracted with DCM. Combined organic layer was dried with anhydrous sodium sulfate, filtered and concentrated in vacuo to give compound 2.8.1a (0.85 g) which was used for the next step without further purification. MS m/z (M+Na) 336.3

Workup

  1. customthe reaction was quenched with 1.0 M sulfuric acid
  2. extractionextracted with DCM
  3. dry with materialCombined organic layer was dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give compound 2.8.1a (0.85 g) which
  7. customwas used for the next step without further purification

Sources & evidence

ORD record
ord-1054c6d287df40a7a5042d364f746a4e
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

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