Sodium borohydride → 5-(2-hydroxyethoxy)-5-(1-trityl-1H-imidazol-4-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1095446Notes

Reaction equation

[BH4-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([C:22]1[N:23]=[CH:24][N:25]([C:27]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:26]=1)([O:15][CH2:16][C:17](OCC)=[O:18])[CH2:10][CH2:9][CH2:8]2)#[N:4]>C(O)C>[OH:18][CH2:17][CH2:16][O:15][C:11]1([C:22]2[N:23]=[CH:24][N:25]([C:27]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:26]=2)[CH2:10][CH2:9][CH2:8][C:7]2[CH:6]=[C:5]([C:3]#[N:4])[CH:14]=[CH:13][C:12]1=2

Participants

Conditions

Temperature: 20 °C

Procedure

3.0 mmol of sodium borohydride are added in portions to a solution of 1.0 mmol of ethyl [6-cyano-1-(1-trityl-1H-imidazol-4-yl)-1,2,3,4-tetrahydronaphthalen-1-yloxy]acetate in 5 ml of ethanol at 20° C. The reaction mixture is stirred at 20° C. for 2-6 hours and then evaporated. The residue is taken up in saturated aqueous sodium bicarbonate solution and dichloromethane, and the mixture is vigorously stirred for 10 minutes. The phases are separated and the aqueous phase is back-extracted with dichloromethane. The combined organic phases are dried with sodium sulphate and evaporated. The title compound is identified from the residue on the basis of its Rf by flash chromatography (SiO2 60F).

Workup

customevaporated
stirringdichloromethane, and the mixture is vigorously stirred for 10 minutes
customThe phases are separated
extractionthe aqueous phase is back-extracted with dichloromethane
dry with materialThe combined organic phases are dried with sodium sulphate
customevaporated

Sources & evidence

ORD record: ord-acebce3118a2471b93179e486f86a6d3
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138179B2

Reaction notes

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