Acetic Acid → HCID 23047421, compound

HRID 2107079Notes

Reaction equation

HRID 2107079 reaction equation
[BH4-].[Na+].[OH:3][CH:4]([CH2:14][CH2:15][C:16]1[C:17]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][N:19]2[C:28]=1[CH:29]([CH3:31])[CH3:30])[CH2:5][C:6](=[O:13])[CH2:7][C:8]([O:10]CC)=[O:9].[OH-].[Na+].C(O)(=O)C>CO.O>[OH:13][CH:6]([CH2:5][CH:4]([OH:3])[CH2:14][CH2:15][C:16]1[C:17]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][N:19]2[C:28]=1[CH:29]([CH3:30])[CH3:31])[CH2:7][C:8]([OH:10])=[O:9]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 23047442HCID 23047442, compound

Product 1

HCID 23047421HCID 23047421, compoundYield 101.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Sodium borohydride (38 mg) was added to a stirred solution of ethyl 5-hydroxy-7-(3-isopropyl-1-phenylpyrrolo[2,1-a]isoquinolin-2-yl)-3-oxoheptanoate (760 mg; prepared as described in Reference Example 3) in methanol (20 ml) at 0° C. under an argon atmosphere. The mixture was stirred at 30 minutes and then a solution of sodium hydroxide (320 mg) in water (8 ml) was added and the mixture was stirred for 1 hour. The mixture was then diluted with water (20 ml) and acidified with glacial acetic acid. The resulting milky solution was extracted with diethyl ether (3×50 ml) and the combined extracts were dried over magnesium sulphate and evaporated, to give 3,5-dihydroxy-7-(3-isopropyl-1-phenylpyrrolo[2,1-a]-isoquinolin-2-yl)heptanoic acid (730 mg), in the form of a yellow gum.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. extractionThe resulting milky solution was extracted with diethyl ether (3×50 ml)
  3. dry with materialthe combined extracts were dried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-9eef80ba4a9b4c9896394a5b55ba9b42
Source dataset
uspto-grants-1990_06
Patent number
US04933350

Reaction notes

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