Sodium Cyanide → HCID 90408367, compound

HRID 1855070Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:15]23[CH2:22][CH2:21][C:18]([CH2:23]I)([CH2:19][CH2:20]2)[CH2:17][O:16]3)[CH:5]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH:7]=1.C1OCCOCCOCCOCCOCCOC1.[C-:43]#[N:44].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:15]23[CH2:22][CH2:21][C:18]([CH2:23][C:43]#[N:44])([CH2:19][CH2:20]2)[CH2:17][O:16]3)[CH:5]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 1-(3-fluoro-5-(tetrahydro-2H-pyran-2-yloxy)phenyl)-4-(iodomethyl)-2-oxabicyclo[2.2.2]octane (732 mg, 1.640 mmol), 18-crown-6 (43 mg, 0.164 mmol), and NaCN (88 mg, 1.80 mmol) in DMF (1 mL) was stirred at 40° C. under N2 for 18 h. The reaction was cooled to rt and filtered. The filtrate was concentrated in vacuo. The residue was taken up in DCM (50 mL) and filtered. The residual solid was washed with DCM (10 mL×2). The combined organic filtrates were concentrated in vacuo. The crude oil was purified by flash chromatography (SiO2) using a 0% to 30% EtOAc/hexane gradient (15 min) to give the title compound (560 mg, 1.62 mmol, 99% yield) as a white solid.

Workup

temperatureThe reaction was cooled to rt
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
filtrationfiltered
washThe residual solid was washed with DCM (10 mL×2)
concentrationThe combined organic filtrates were concentrated in vacuo
customThe crude oil was purified by flash chromatography (SiO2)
customa 0% to 30% EtOAc/hexane gradient (15 min)

Sources & evidence

ORD record: ord-247ccfec3976441eb434ba13d1f1bfa5
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962660B2

Reaction notes

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