Magnesium → 6(S)-Tert-butoxycarbonylamino-5(S)-hydroxy-3(R,S)-isopropyl-10-triisopropylsilyloxy-8,8-dimethyldec-1-ene

HRID 863236Notes

Reaction equation

HRID 863236 reaction equation
Br[CH2:2][CH:3]([CH:6]([CH3:8])[CH3:7])[CH:4]=[CH2:5].[Mg].[C:10]([O:14][C:15]([NH:17][C@@H:18]([CH2:21][C:22]([CH3:37])([CH3:36])[CH2:23][CH2:24][O:25][Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])[CH:19]=[O:20])=[O:16])([CH3:13])([CH3:12])[CH3:11]>>[C:10]([O:14][C:15]([NH:17][C@@H:18]([CH2:21][C:22]([CH3:36])([CH3:37])[CH2:23][CH2:24][O:25][Si:26]([CH:27]([CH3:29])[CH3:28])([CH:30]([CH3:31])[CH3:32])[CH:33]([CH3:34])[CH3:35])[C@@H:19]([OH:20])[CH2:2][CH:3]([CH:6]([CH3:8])[CH3:7])[CH:4]=[CH2:5])=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 3

HCID 5462224MagnesiumHCID 10631133(RS)-2-isopropyl-3-butenyl bromideHCID 228823952(S)-Tert-butoxycarbonylamino-6-triisopropylsilyloxy-4,4-dimethyl-hexanal

Product 1

HCID 228825816(S)-Tert-butoxycarbonylamino-5(S)-hydroxy-3(R,S)-isopropyl-10-triisopropylsilyloxy-8,8-dimethyldec-1-ene

Procedure

The title compound is prepared in a manner analogous to that described in Example 35f) starting from 23.9 g of 1-bromo-2(R,S)-isopropyl-3-butene (preparation according to D. Mesnard et al., C.R. Acad. Sci. Paris, t. 277, Series C-567), 3.3 g of magnesium powder and 11.25 g of 2(S)-tert-butoxycarbonylamino-6-triisopropylsilyloxy-4,4-dimethyl-hexanal (Example 1g). The crude product is purified by FC over 900 g of silica gel (mobile phase E) to give the title compound as a diastereomer mixture: Rf (E)=0.31.

Workup

  1. customThe title compound is prepared in a manner analogous to
  2. customThe crude product is purified by FC over 900 g of silica gel (mobile phase E)

Sources & evidence

ORD record
ord-44ffebc66a794361b59a6e57bfd8da36
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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