Tetrabutylammonium Fluoride → HCID 58968741, compound

HRID 2075112Notes

Reaction equation

HRID 2075112 reaction equation
[CH3:1][O:2][C:3]1([C:10]2[CH:47]=[CH:46][C:45]([C:48]([F:51])([F:50])[F:49])=[CH:44][C:11]=2[CH2:12][N:13]([CH2:29][C:30]2[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[C:32]([C:40]([F:43])([F:42])[F:41])[CH:31]=2)[C:14]2[N:15]=[N:16][N:17]([CH2:19][CH2:20][O:21][Si](C(C)(C)C)(C)C)[N:18]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CC1CCCO1>[CH3:1][O:2][C:3]1([C:10]2[CH:47]=[CH:46][C:45]([C:48]([F:51])([F:49])[F:50])=[CH:44][C:11]=2[CH2:12][N:13]([CH2:29][C:30]2[CH:35]=[C:34]([C:36]([F:37])([F:38])[F:39])[CH:33]=[C:32]([C:40]([F:42])([F:41])[F:43])[CH:31]=2)[C:14]2[N:15]=[N:16][N:17]([CH2:19][CH2:20][OH:21])[N:18]=2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58968627HCID 58968627, compound

Product 1

HCID 58968741HCID 58968741, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent

Procedure

To a solution of N-(2-(1-methoxycycloheptyl)-5-(trifluoromethyl)benzyl)-N-(3,5-bis(trifluoromethyl)benzyl)-2-(2-(tert-butyldimethylsilyloxy)ethyl)-2H-tetrazol-5-amine (42 mg, 0.056 mmol) in 2-methyltetrahydrofuran (1.5 mL) was added tetrabutylammonium fluoride (0.1 mL; 0.1 mmol; 1.0M in tetrahydrofuran). Reaction was stirred at room temperature for 1.5 hours. The reaction was concentrated in vacuo. The residue was purified by 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 10-40% ethyl acetate in heptane) to give 34 mg (95% yield) of a gum. MS (ES+): Calc: 639.5, Found: 640.5 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 7.78 (s, 1H), 7.74 (s, 2H), 7.45 (m, 3H), 5.10 (s, 2H), 4.81 (s, 2H), 4.61 (t, J=4.98 Hz, 2H), 4.11 (q, J=6.22, 5.8 Hz 1, 2H), 2.94 (s, 3H), 2.44 (t, J=6.64, 6.22 Hz, 1H), 2.11 (m, 2H), 2.19 (m, 2H), 1.82-1.45(m, 8H).

Workup

  1. customReaction
  2. concentrationThe reaction was concentrated in vacuo
  3. customThe residue was purified by 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 10-40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-650c2ef2805d460d83d2fa2138344736
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

Loading…