Water → HCID 57904997, compound

HRID 1093060Notes

Reaction equation

[Si]([O:8][CH2:9][CH:10]1[CH2:14][CH2:13][CH:12]([CH:15]([C:28]#[N:29])[N:16]([CH3:27])[C:17](=[O:26])[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:11]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[C:28]([CH:15]([CH:12]1[CH2:13][CH2:14][CH:10]([CH2:9][OH:8])[CH2:11]1)[N:16]([CH3:27])[C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)#[N:29]

Participants

Conditions

Temperature: 23 °C

Procedure

To benzyl (3-((tert-butyldimethylsilyloxy)methyl)cyclopentyl)(cyano)methyl(methyl)-carbamate (2.0 g, 4.80 mmol) in dry THF (40 mL) cooled to 0° C. was added tetrabutyl-ammoniumfluoride (1M in THF 17.28 mL). The reaction mixture was stirred at 23° C. for 5 hours. H2O (20 mL) was added to the reaction mixture and the organic material extracted with ethyl acetate (3×30 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo. The crude material was purified on a Silica gel column (Biotage flash chromatography system), eluted with a gradient of ethyl acetate:hexane (3:7) to ethyl acetate 100% to afford 0.550 g (38% yield) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.39 (5 H, m), 5.13-5.25 (2 H, m), 5.07 (1 H, br s), 3.50-3.60 (2 H, m), 3.01 (3 H, s), 1.30-2.52 (8 H, m). LCMS (+ESI, M+H+) m/z 303.

Workup

extractionthe organic material extracted with ethyl acetate (3×30 mL)
dry with materialThe combined organic fractions were dried (MgSO4)
concentrationconcentrated in vacuo
customThe crude material was purified on a Silica gel column (Biotage flash chromatography system)
washeluted with a gradient of ethyl acetate:hexane (3:7) to ethyl acetate 100%

Sources & evidence

ORD record: ord-57841db347b94589b20c2825b16d7615
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129398B2

Reaction notes

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