Tetrabutylammonium Fluoride → HCID 178482461, compound

HRID 1641304Notes

Reaction equation

HRID 1641304 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[C:11]([NH:25][CH2:26][Si](C)(C)C)=[N:10][C:9]2=[O:31])[CH:5]=[CH:6][CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:14][CH2:13]3)[C:11]([NH:25][CH3:26])=[N:10][C:9]2=[O:31])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178451557HCID 178451557, compound

Product 1

HCID 178482461HCID 178482461, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a 50 ml THF solution of 1.04 g (2.41 mmol) tert-butyl 1-(3-fluorophenyl)-2-oxo-4-{[(trimethylsilyl)methyl]amino}-1,3,8-triazaspiro[4.5]dec-3-ene-8-carboxylate (prepared in the same manner as Intermediate 5-1 above) was added 3.61 mL (3.61 mmol) of a 1.0M tetrabutylammonium fluoride in THF solution over 5 m and the reaction warmed to 60° C. overnight. The reaction was concentrated to dryness in vacuo and the residue treated with 100 mL CH2Cl2. The organic layer was washed with water (1×25 mL), brine (1×25 mL), dried over Na2SO4, filtered and concentrated to dryness in vacuo to give a crude oil (1.6 g). Purification by flash chromatography (0-7.5% MeOH in CH2Cl2 over 25 m) afforded tert-butyl 1-(3-fluorophenyl)-4-(methylamino)-2-oxo-1,3,8-triazaspiro[4.5]dec-3-ene-8-carboxylate 6-2 as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.39 (m, 1H), 7.12 (m, 1H), 7.03 (d, J=7.95 Hz, 1H), 6.97 (m, 1H), 5.70 (br s, 1H), 3.54 (m, 2H), 3.11 (d, J=4.76 Hz, 3H), 2.02 (m, 2H), 1.92 (m, 2H), 1.42 (s, 9H). High resolution mass spec (FT/ICR): calc M+H=377.1984. found 377.2010

Workup

  1. concentrationThe reaction was concentrated to dryness in vacuo
  2. additionthe residue treated with 100 mL CH2Cl2
  3. washThe organic layer was washed with water (1×25 mL), brine (1×25 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness in vacuo
  7. customto give a crude oil (1.6 g)
  8. customPurification by flash chromatography (0-7.5% MeOH in CH2Cl2 over 25 m)

Sources & evidence

ORD record
ord-0bc3807974b54b43814c0a1ee3af16d7
Source dataset
uspto-grants-2012_02
Patent number
US08114887B2

Reaction notes

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