Sodium borohydride → HCID 23166913, compound

HRID 1087734Notes

Reaction equation

HRID 1087734 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](/[CH:24]=[CH:25]/[CH:26]([OH:36])[CH2:27][C:28](=[O:35])[CH2:29][C:30]([O:32][CH2:33]C)=[O:31])=[C:10]([CH:21]([CH3:23])[CH3:22])[N:11]3[N:20]=[CH:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]=23)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](/[CH:24]=[CH:25]/[CH:26]([OH:36])[CH2:27][CH:28]([OH:35])[CH2:29][C:30]([O:32][CH3:33])=[O:31])=[C:10]([CH:21]([CH3:23])[CH3:22])[N:11]3[N:20]=[CH:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]=23)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86744241HCID 86744241, compound

Product 1

HCID 23166913HCID 23166913, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of ethyl (E)-7-{1-(4-fluorophenyl)-3-isopropylpyrrolo[2,1-a]phthalazin-2-yl}-5- hydroxy-3-oxohept-6-enoate (3.98 g) in methanol (120 ml) under an argon atmosphere at 0°-5° C. was treated with sodium borohydride (243 mg). After 3 hours the solution was allowed to warm to room temperature, and was then evaporated to small volume (20 ml). The solution was treated with water (300 ml), and extracted with a mixture of diethyl ether and ethyl acetate (2×250 ml; 1:1 v/v). The combined extracts were dried over magnesium sulphate and evaporated, to give methyl (E)-7-{1-(4-fluorophenyl)-3-isopropylpyrrolo[2,1-a]-phthalazin-2-yl}-3,5-dihydroxyhept-6-enoate, in the form of an orange foam (3.16 g).

Workup

  1. customwas then evaporated to small volume (20 ml)
  2. additionThe solution was treated with water (300 ml)
  3. extractionextracted with a mixture of diethyl ether and ethyl acetate (2×250 ml; 1:1 v/v)
  4. dry with materialThe combined extracts were dried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-57f3267606f5474ca42f7b01c0f8c7cd
Source dataset
uspto-grants-1990_10
Patent number
US04960775

Reaction notes

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