Hydrochloric Acid → 2-[4-(2-Butyl-4-chloro-5-hydroxymethyl-imidazol-1-yl-methyl)phenyl]-2-cyclopentylacetic acid

HRID 1955740Notes

Reaction equation

HRID 1955740 reaction equation
[BH4-].[Na+].[CH2:3]([C:7]1[N:8]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]([CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[C:23]([OH:25])=[O:24])=[CH:18][CH:17]=2)[C:9]([CH:13]=[O:14])=[C:10]([Cl:12])[N:11]=1)[CH2:4][CH2:5][CH3:6].Cl>C(O)C>[CH2:3]([C:7]1[N:8]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([CH:22]([CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[C:23]([OH:25])=[O:24])=[CH:20][CH:21]=2)[C:9]([CH2:13][OH:14])=[C:10]([Cl:12])[N:11]=1)[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 152255902-[4-(2-Butyl-4-chloro-5-formyl-imidazol-1-yl-methyl)-phenyl]-2-cyclopentylacetic acid

Product 1

HCID 190725392-[4-(2-Butyl-4-chloro-5-hydroxymethyl-imidazol-1-yl-methyl)phenyl]-2-cyclopentylacetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.1 g (2.9 mmol) of sodium borohydride is added to 1.5 g (2.9 mmol) of the compound from Example V in 25 ml of ethanol. After 1 h at room temperature, the reaction mixture is acidified (pH 4) with 2N HCl and extracted three times with CH2Cl2. The organic phase is dried over Na2SO4 and concentrated, and the product is crystallised from ethyl acetate/petroleum ether. A 1:1 mixture of the diastereomers is obtained.

Workup

  1. extractionextracted three times with CH2Cl2
  2. dry with materialThe organic phase is dried over Na2SO4
  3. concentrationconcentrated
  4. customthe product is crystallised from ethyl acetate/petroleum ether
  5. additionA 1:1 mixture of the diastereomers
  6. customis obtained

Sources & evidence

ORD record
ord-048a276b26194373a82a2426bb4f2161
Source dataset
uspto-grants-1998_07
Patent number
US05776964

Reaction notes

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