Diisobutylaluminumhydride → 3-[(5-tert-butyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)methyl]cyclobutane-1-carbaldehyde

HRID 2040673Notes

Reaction equation

HRID 2040673 reaction equation
[C:1]([C:5]1[CH:32]=[CH:31][C:8]2[N:9]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:10]([CH2:12][CH:13]3[CH2:16][CH:15]([C:17](N(OC)C)=[O:18])[CH2:14]3)=[N:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1.C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:32]=[CH:31][C:8]2[N:9]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:28])([CH3:29])[CH3:30])[C:10]([CH2:12][CH:13]3[CH2:16][CH:15]([CH:17]=[O:18])[CH2:14]3)=[N:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 866661233-[(5-tert-butyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)methyl]-N-methoxy-N-methylcyclobutane-1-carboxamide

Product 1

HCID 866661243-[(5-tert-butyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)methyl]cyclobutane-1-carbaldehydeYield 130.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[(5-tert-butyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)methyl]-N-methoxy-N-methylcyclobutane-1-carboxamide (0.61 g, 1.32 mmol) in tetrahydrofuran (15 ml) was added dropwise 1M diisobutylaluminum hydride solution in toluene (3.29 ml) under N2 at −10° C. The reaction was stirred at this temperature for 2.5 h before being quenched by the addition of methanol (2 ml) and stirred for 5 mins. The solution was poured onto saturated aq. Rochelle's salt (20 ml), diluted with Et2O (30 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 nil). This was dried (MgSO4) and concentrated to afford the title compound (0.69 g, 130%) as a colourless gum which was used crude in the next reaction.

Workup

  1. custombefore being quenched by the addition of methanol (2 ml)
  2. stirringstirred for 5 mins
  3. additionThe solution was poured onto saturated aq. Rochelle's salt (20 ml)
  4. additiondiluted with Et2O (30 ml)
  5. stirringstirred for 30 min
  6. customThis was then separated
  7. washthe organic layer was washed with Rochelle's salt (30 ml), sat. NaHCO3 (30 ml), and brine (30 nil)
  8. dry with materialThis was dried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1761569ab56e45c6831b29c4df6dc697
Source dataset
uspto-grants-2013_11
Patent number
US08580762B2

Reaction notes

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