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

HRID 863237Notes

Reaction equation

HRID 863237 reaction equation
Br[CH2:2][CH:3]([CH:6]([CH3:8])[CH3:7])[CH:4]=[CH2:5].[Mg].[CH2:10]([O:17][CH2:18][CH2:19][C:20]([CH3:34])([CH3:33])[CH2:21][C@H:22]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:23]=[O:24])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([O:17][CH2:18][CH2:19][C:20]([CH3:34])([CH3:33])[CH2:21][C@H:22]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@@H:23]([OH:24])[CH2:2][CH:3]([CH:6]([CH3:8])[CH3:7])[CH:4]=[CH2:5])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 5462224MagnesiumHCID 10631133(RS)-2-isopropyl-3-butenyl bromideHCID 228825796-Benzyloxy-2(S)-tert-butoxycarbonylamino-4,4-dimethyl-hexanal

Product 1

HCID 2288234410-Benzyloxy-6(S)-tert-butoxycarbonylamino-5(S)-hydroxy-3(R,S)-isopropyl-8,8-dimethyldec-1-ene

Procedure

88.5 g of 1-bromo-2(R,S)-isopropyl-3-butene, 13 g of magnesium powder and 41.9 g of 6-benzyloxy-2(S)-tert-butoxycarbonylamino-4,4-dimethyl-hexanal are reacted in a manner analogous to that described in Example 37f). Purification is carried out by FC over 1 kg of silica gel (mobile phases G and E): Rf (3:1 mixture of toluene and ethyl acetate)=0.47; Rt (I)=33.8/34.2 min; FAB-MS: (M+H)+ =520.

Workup

  1. customPurification
  2. additionRf (3:1 mixture of toluene and ethyl acetate)=0.47
  3. custom34.2 min

Sources & evidence

ORD record
ord-e2b1cb1c09e448dbaad75763a816e9cc
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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