Diisobutylaluminumhydride → 2(S)-tert-butoxycarbonylamino-4(S)-methyl-6-triisopropylsilyloxyhexanal

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.

1. customThe reaction is then quenched by rapid addition of 2.8 ml of methanol
2. additionthe mixture is poured onto 50 ml of a half-saturated aqueous potassium sodium tartrate solution
3. extractionThe mixture is extracted with diethyl ether
4. dry with materialthe combined organic phases are dried over sodium sulfate
5. concentrationconcentrated
6. customThe title compound (Rf (E)=0.34) is further reacted directly as the crude product

ORD record

ord-2ec12b3fe2784035b4ba6ad867af0864

Source dataset

uspto-grants-1998_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05719141