Diisobutylaluminumhydride → HCID 86760334, compound

HRID 857969Notes

Reaction equation

HRID 857969 reaction equation
C[O:2][C:3](=O)/[CH:4]=[CH:5]\[C@H:6]([CH3:47])[C@H:7]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[C@@H:8]([CH3:38])[CH2:9][N:10]([C:12](=[O:37])[C@H:13]([CH3:36])[C@@H:14]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[C@H:15]([CH3:27])[C@@H:16]([O:23][C:24]([NH2:26])=[O:25])[C@@H:17]([CH3:22])/[CH:18]=[CH:19]\[CH:20]=[CH2:21])[CH3:11].[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[NH2:26][C:24]([O:23][C@@H:16]([C@@H:17]([CH3:22])/[CH:18]=[CH:19]\[CH:20]=[CH2:21])[C@@H:15]([CH3:27])[C@H:14]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:30])[CH3:31])[C@@H:13]([CH3:36])[C:12]([N:10]([CH2:9][C@H:8]([CH3:38])[C@@H:7]([O:39][Si:40]([C:43]([CH3:44])([CH3:46])[CH3:45])([CH3:41])[CH3:42])[C@@H:6]([CH3:47])/[CH:5]=[CH:4]\[CH2:3][OH:2])[CH3:11])=[O:37])=[O:25]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86760332HCID 86760332, compound

Product 1

HCID 86760334HCID 86760334, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (2Z,4S,5S,6S)-7-[[(2R,3S,4R,5S,6S,7Z)-5-[(aminocarbonyl)oxy]-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2,4,6-trimethyl-1-oxo-7,9-decadienyl]methylamino]-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,6-dimethyl-2-heptenoic acid methyl ester (1.77 g, 2.5 mmol) and CH2Cl2 (15 mL) cooled to −78° C., was added a solution consisting of diisobutylaluminum hydride (1.0 M in hexane, 7.5 mL, 7.5 mmol). After stirring at 40° C. for 4 h, the mixture is quenched by adding saturated potassium sodium tartrate (10 mL). The mixture is then extracted with CH2Cl2 (3×20 mL). The combined organic layers are then dried (Na2SO4), concentrated in vacuo, and chromatographed using silica gel eluted with hexane/EtOAc (70/30) to give the desired compound (1.04 mg, 61.4%) as a colorless glassy solid.

Workup

  1. additionwas added a solution
  2. customthe mixture is quenched
  3. additionby adding saturated potassium sodium tartrate (10 mL)
  4. extractionThe mixture is then extracted with CH2Cl2 (3×20 mL)
  5. dry with materialThe combined organic layers are then dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customchromatographed
  8. washeluted with hexane/EtOAc (70/30)

Sources & evidence

ORD record
ord-0d7412dfba924d4085c572c3e204cd03
Source dataset
uspto-grants-2006_12
Patent number
US07148218B2

Reaction notes

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