Diisobutylaluminumhydride → 2(S)-tert-butoxycarbonylamino-4(S)-methyl-6-triisopropylsilyloxyhexanal
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C@H:15]([CH3:29])[CH2:16][CH2:17][O:18][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C@H:15]([CH3:29])[CH2:16][CH2:17][O:18][Si:19]([CH:20]([CH3:22])[CH3:21])([CH:23]([CH3:25])[CH3:24])[CH:26]([CH3:27])[CH3:28])[CH:10]=[O:11])=[O:7])([CH3:3])([CH3:4])[CH3:2]Participants
4
Conditions
- Temperature
- -75 °C
Procedure
A solution of 3.35 g methyl 2(S)-tert-butoxycarbonylamino-4(S)-methyl-6-triisopropylsilyloxyhexanoate in 44 ml of toluene is cooled to -75° C. under argon, and 12.9 ml of a 20% solution of diisobutylaluminium hydride in toluene are then added dropwise in the course of 30 min. The mixture is stirred at -75° C. for a further 45 min. The reaction is then quenched by rapid addition of 2.8 ml of methanol and the mixture is poured onto 50 ml of a half-saturated aqueous potassium sodium tartrate solution. The mixture is extracted with diethyl ether and the combined organic phases are dried over sodium sulfate and concentrated. The title compound (Rf (E)=0.34) is further reacted directly as the crude product.
Workup
- customThe reaction is then quenched by rapid addition of 2.8 ml of methanol
- additionthe mixture is poured onto 50 ml of a half-saturated aqueous potassium sodium tartrate solution
- extractionThe mixture is extracted with diethyl ether
- dry with materialthe combined organic phases are dried over sodium sulfate
- concentrationconcentrated
- customThe title compound (Rf (E)=0.34) is further reacted directly as the crude product
Sources & evidence
- ORD record
- ord-2ec12b3fe2784035b4ba6ad867af0864
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05719141
Reaction notes
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