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Hydrochloric Acid → tert-Butyl 2-[4-(2-butyl-4-chloro-5-hydroxymethyl-imidazol-1-yl-methyl)phenyl]-2-cyclopentylacetate

HRID 1955742
Notes
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Reaction equation

HRID 1955742 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:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[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>CCO>[CH2:3]([C:7]1[N:8]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([CH:22]([CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34]3)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 15225591tert-Butyl 2-[4-(2-butyl-4-chloro-5-formyl-imidazol-1-yl-methyl)phenyl]-2-cyclopentylacetate

Product 1

HCID 19072492tert-Butyl 2-[4-(2-butyl-4-chloro-5-hydroxymethyl-imidazol-1-yl-methyl)phenyl]-2-cyclopentylacetate

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Conditions

Temperature
25 °C

Procedure

265 mg (7 mmol) of sodium borohydride are added to 3.2 g (7 mmol) of the compound from Example I in 30 ml of EtOH and the mixture is stirred at 25° C. for 1 h. After addition of dilute HCl (pH 6), the mixture is extracted three times with CH2Cl2, the organic phase is dried over Na2SO4 and concentrated, and the residue is chromatographed on silica gel 60 using petroleum ether/ethyl acetate (1:1).

Workup

  1. extractionthe mixture is extracted three times with CH2Cl2
  2. dry with materialthe organic phase is dried over Na2SO4
  3. concentrationconcentrated
  4. customthe residue is chromatographed on silica gel 60 using petroleum ether/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-5ba033133f494f9a902baaa217621160
Source dataset
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05776964

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes