Diisobutylaluminum hydride → HCID 59644075, compound
Reaction equation
C([C@@H]1CSC(=S)N1[C:10](=[O:26])[CH2:11][C@H:12]([O:18][Si:19]([CH2:24][CH3:25])([CH2:22][CH3:23])[CH2:20][CH3:21])[CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17])(C)C.CC(C[AlH]CC(C)C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1(C)C=CC=CC=1>[CH2:24]([Si:19]([CH2:20][CH3:21])([CH2:22][CH3:23])[O:18][C@H:12]([CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17])[CH2:11][CH:10]=[O:26])[CH3:25]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
The title compound from Example 7 (6.08 g, 14.2 mmol) was dissolved in toluene (70 mL) under an atmosphere of nitrogen and the mixture was cooled to −78° C. DIBAL (1 M in hexane, 32 mL, 32 mmol) was added over 10 min, and the mixture was stirred at −78° C. for 30 min. The reaction mixture was poured onto half-saturated sodium potassium tartrate solution at 0° C. and stirred for 3 h. The phases were separated and the aqueous phase was extracted twice with 1:9 ethyl acetate/hexanes. The combined organic phases were dried and evaporated, and the residue was diluted with hexane. The resulting solid was filtered off and the filtrate was concentrated and filtered through a silica plug to provide the title compound (3.40 g, 93%) as an oil.
Workup
- stirringstirred for 3 h
- customThe phases were separated
- extractionthe aqueous phase was extracted twice with 1:9 ethyl acetate/hexanes
- customThe combined organic phases were dried
- customevaporated
- additionthe residue was diluted with hexane
- filtrationThe resulting solid was filtered off
- concentrationthe filtrate was concentrated
- filtrationfiltered through a silica plug
Sources & evidence
- ORD record
- ord-4786a24087b54c5bad9b6e64c7f4f24f
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08039465B2
Reaction notes
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