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

HRID 1955742Notes

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]

Participants

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

extractionthe mixture is extracted three times with CH2Cl2
dry with materialthe organic phase is dried over Na2SO4
concentrationconcentrated
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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