Diisobutylaluminum hydride → HCID 68613149, compound

HRID 2095306Notes

Reaction equation

HRID 2095306 reaction equation
CC(C[AlH]CC(C)C)C.C[O:11][C:12](=O)/[CH:13]=[CH:14]/[CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([C@@H:22]2[CH2:25][CH2:24][N:23]2[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:21]=1>C(Cl)Cl>[C:29]([O:28][C:26]([N:23]1[CH2:24][CH2:25][C@H:22]1[C:20]1[CH:21]=[C:16]([CH2:15]/[CH:14]=[CH:13]/[CH2:12][OH:11])[CH:17]=[N:18][CH:19]=1)=[O:27])([CH3:32])([CH3:31])[CH3:30]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 68613266HCID 68613266, compound

Product 1

HCID 68613149HCID 68613149, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

DIBAL-H (1.5M in toluene, 4.9 mL, 7.35 mmol, 2.7 equiv.) was added dropwise to a stirred solution of 4-[5-[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]-3-pyridyl]-trans-2-butenoic acid methyl ester (1.00 g, 2.75 mmol) in dry CH2Cl2 at −78° C. The mixture was stirred at −78° C. for 3 hours before the reaction was quenched by adding methanol followed by saturated aqueous sodium potassium tartrate solution. The reaction mixture was then allowed to warm to room temperature where it was vigorously stirred for 1 h. The organic layer was separated, and the aqueous layer was extracted three times with CH2Cl2. The combined organic layers were washed with brine and dried over Na2SO4. Filtration and solvent removal afforded the crude product, which was purified by CC (SiO2, 3% methanol in CH2Cl2) to give the title alcohol as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ 8.17 (s, 2H), 7.24 (s, 1H), 6.60 (d, J=18.2 Hz, 1H), 6.38 (m, 1H) 4.49 (m, 1H), 4.33 (m, 1H), 4.10 (dd, J=6.1, 3.2 Hz, 1H), 3.62 (t, J=6.1 Hz, 2H), 3.20 (1H, OH), 2.31 (m, 2H), 1.39 (s, 9H); 13C NMR (CDCl3, 100 MHz) δ 156.4, 155.0, 155.0, 140.4, 136.3, 133.3, 125.5, 117.8, 79.5, 71.4, 68.4, 59.9, 46.9, 43.5, 28.3, 18.7; MS (ESI) 335 (M+H+).

Workup

  1. customwas quenched
  2. additionby adding methanol
  3. temperatureto warm to room temperature where it
  4. stirringwas vigorously stirred for 1 h
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted three times with CH2Cl2
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationFiltration and solvent removal
  10. customafforded the crude product, which
  11. customwas purified by CC (SiO2, 3% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-9c31ab75a82a42bd9b27066bf46a87aa
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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