Sodium Cyanide → HCID 86610916, compound

HRID 2377042Notes

Reaction equation

HRID 2377042 reaction equation
[I-].[F:2][C:3]([F:41])([F:40])[C:4]1[CH:5]=[C:6]([C@H:14]([O:16][C@@H:17]2[C@@H:21]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH2:20][N:19]([C:29]3[CH2:33][CH2:32][C:31](=[O:34])[C:30]=3[CH2:35][N+](C)(C)C)[CH2:18]2)[CH3:15])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1.[C-:42]#[N:43].[Na+]>C(O)C>[F:2][C:3]([F:40])([F:41])[C:4]1[CH:5]=[C:6]([C@H:14]([O:16][C@@H:17]2[C@@H:21]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH2:20][N:19]([C:29]3[CH2:33][CH2:32][C:31](=[O:34])[C:30]=3[CH2:35][C:42]#[N:43])[CH2:18]2)[CH3:15])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 86610914HCID 86610914, compound

Product 1

HCID 86610916HCID 86610916, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 32 mg (0.0394 mmol) {2-[(3R,4S)-3-({(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethyl}oxy)-4-(4-fluorophenyl)pyrrolidin-1-yl]-5-oxocyclopent-1-en-1-yl}-N,N,N-trimethylmethanaminium iodide (step B) and 41.7 mg (0.8505 mmol) sodium cyanide in 95% ethanol (5 mL) was refluxed for 6 hr. The reaction mixture was cooled to RT and the solvent removed under vacuum. The residue was purified by prep TLC on silica gel eluting with methylene chloride/methanol (9/1). The UV active band (Rf˜0.4) was isolated to afford the title compound as a glassy yellow solid. 1H-NMR (CD3OD): δ: 1.45 (d, 3H, 6.5 Hz), 2.43 (br. s, 2H), 2.79 (br. s, 2H), 3.4-4.55 (m, 8H), 4.79 (q, 1H, 6.5 Hz), 6.99 (t, 2H, 8.5 Hz), 7.20 (m, 2H), 7.72 (s, 2H), 7.83 (s, 1H)ppm. MS: 541.0 (MH+) observed.

Workup

  1. customthe solvent removed under vacuum
  2. customThe residue was purified by prep TLC on silica gel eluting with methylene chloride/methanol (9/1)
  3. customThe UV active band (Rf˜0.4) was isolated

Sources & evidence

ORD record
ord-251fdfd5a50c425fa9fb0c46d190c3f3
Source dataset
uspto-grants-2008_12
Patent number
US07468437B2

Reaction notes

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