Potassium Sodium Tartrate → 3-{[5-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl]methyl}cyclobutane-1-carbaldehyde

HRID 2040662Notes

Reaction equation

HRID 2040662 reaction equation
CC(C[AlH]CC(C)C)C.CON(C)[C:13]([CH:15]1[CH2:18][CH:17]([CH2:19][C:20]2[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:23]3[CH:33]=[CH:34][C:35]([C:37]([F:40])([F:39])[F:38])=[CH:36][C:22]=3[N:21]=2)[CH2:16]1)=[O:14].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.CCOCC>[F:40][C:37]([F:38])([F:39])[C:35]1[CH:34]=[CH:33][C:23]2[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:31])[CH3:32])[C:20]([CH2:19][CH:17]3[CH2:18][CH:15]([CH:13]=[O:14])[CH2:16]3)=[N:21][C:22]=2[CH:36]=1

Participants

6

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 86666119N-methoxy-N-methyl-3-{[5-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl]methyl}cyclobutane-1-carboxamide

Product 1

HCID 866661163-{[5-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl]methyl}cyclobutane-1-carbaldehydeYield 87%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

DIBAL (0.69 ml, 0.69 mmol, 1M in THF) was added dropwise to a solution of N-methoxy-N-methyl-3-{[5-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl]methyl}cyclobutane-1-carboxamide in THF at −10° C. whilst stirring. The reaction was continued for 3 hours at −10° C. The reaction mixture was poured onto sat. aq. Rochelle's salt (20 ml), diluted with Et2O (50 ml) and stirred for 30 min. This was then separated and the organic layer was washed with Rochelle's salt (30 ml), sat. NaHCO3, (30 ml) and brine (30 ml). This was dried over Na2SO4, filtered and evaporated to give a colorless gum (190 mg, 87%); MS (ESI+) for C20H27F3N2O2Si m/z 413.6 [M+H]+; HPLC purity 87% (ret. time, 2.25 min); 1H NMR (500 MHz, CHLOROFORM-d) δH ppm −0.10-0.09 (9 H, m), 0.88-1.00 (4 H, m), 1.63-1.97 (2 H, m), 2.07-2.23 (2 H, m), 2.24-2.37 (0 H, m), 2.37-2.42 (1 H, m), 2.43-2.66 (2 H, m), 2.93-3.34 (4 H, m), 5.49-5.61 (2 H, m), 7.16-7.31 (2 H, m), 7.32-7.32 (2 H, m), 7.49-7.61 (1 H, m), 7.73 (1 H, s), 7.83 (1 H, d, J=8.35 Hz).

Workup

  1. stirringstirred for 30 min
  2. customThis was then separated
  3. washthe organic layer was washed with Rochelle's salt (30 ml), sat. NaHCO3, (30 ml) and brine (30 ml)
  4. dry with materialThis was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-44b64c607cfd4c5c949cc256938ab74d
Source dataset
uspto-grants-2013_11
Patent number
US08580762B2

Reaction notes

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