Pivalic acid → HCID 86743385, compound

HRID 1607898Notes

Reaction equation

HRID 1607898 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]=[CH:15][CH:16]([OH:26])[CH2:17][C:18](=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:12]([CH3:27])[N:11]=[C:10]([CH3:28])[N:9]=2)=[CH:4][CH:3]=1.C(O)(=O)C(C)(C)C.C(B(CC)CC)C.[BH4-].[Na+]>O1CCCC1.O.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]=[CH:15][CH:16]([OH:26])[CH2:17][CH:18]([OH:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:12]([CH3:27])[N:11]=[C:10]([CH3:28])[N:9]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6417Pivalic acidHCID 7357TriethylboraneHCID 4311764Sodium borohydrideHCID 86743386HCID 86743386, compound

Product 1

HCID 86743385HCID 86743385, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 27.5 g (0.071 mol) of [R*, S* (E)]-7-[4-(4-fluorophenyl)-2,6-dimethyl-5-pyrimidinyl]-5-hydroxy-3-oxo-6-heptenoic acid, ethyl ester and 0.73 g (0.0071 mol) of pivalic acid in 140 mL of anhydrous tetrahydrofuran under a dry air atmosphere at room temperature was added a 1M solution of triethylborane (28.4 mL, 0.0784 mol) in a dropwise manner. This solution was stirred for five minutes before 20 mL of air was bubbled through the solution. The mixture was thencooled to -78° C. and 18 mL of methanol and 2.96 g (0.0784 mol) of sodium borohydride were added. This mixture was stirred at -78° C. for six hours and then poured into 140 mL of ice cold 30% hydrogen peroxide solution at 0° C. This mixture was stirred at room temperature overnight and then diluted with water and extracted with ethylacetate.

Workup

  1. customwas bubbled through the solution
  2. customwas thencooled to -78° C.
  3. stirringThis mixture was stirred at -78° C. for six hours
  4. stirringThis mixture was stirred at room temperature overnight
  5. extractionextracted with ethylacetate

Sources & evidence

ORD record
ord-6a8bbd4199de4f74a2fb7dad680c3505
Source dataset
uspto-grants-1989_09
Patent number
US04868185

Reaction notes

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