Hexane → HCID 86674107, compound

HRID 1525148Notes

Reaction equation

[NH2:1][C@@:2]1([C:14]([F:18])([F:17])[CH2:15][OH:16])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[CH2:4][CH2:3]1.C([O-])(=O)C.[Na+].[N:24]#[C:25]Br.CCCCCC>C(O)C.C(OCC)(=O)C>[F:18][C:14]([C@:2]1([NH:1][C:25]#[N:24])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[CH2:4][CH2:3]1)([F:17])[CH2:15][OH:16]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 2-((R)-1-amino-6-nitro-indan-1-yl)-2,2-difluoro-ethanol (intermediate A5.6), (1.6 g, 6.2 mmol) and sodium acetate (1.54 g, 18.6 mmol) in ethanol (30 ml) was warmed to 40° C. The mixture was then treated with cyanogen bromide (724 mg, 6.82 mmol) and allowed to stir at 40° C. for 16 hours. Removal of the solvent at reduced pressure followed by purification of the resultant crude material by column chromatography on silica gel using a 3:2-mixture of hexane and ethyl acetate as the eluent yielded the (R)-1-(1,1-difluoro-2-hydroxy-ethyl)-6-nitro-indan-1-yl-cyanamide (800 mg, 42% yield) as colorless sticky solid. MS (ISP): m/z=284.0 [M+H]+.

Workup

customRemoval of the solvent at reduced pressure
customfollowed by purification of the resultant crude material by column chromatography on silica gel using a 3

Sources & evidence

ORD record: ord-605f07a23cb04ece8d61af8c5436fb0b
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079919B2

Reaction notes

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