Allyl bromide → HCID 70087875, compound

HRID 2303453Notes

Reaction equation

HRID 2303453 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH:12]1[C:16](=[O:17])[O:15][CH:14]2[CH2:18][CH:19]=[CH:20][CH:13]12.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:31](Br)[CH:32]=[CH2:33]>C1COCC1>[CH2:33]([C@:12]1([CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[C:16](=[O:17])[O:15][C@H:14]2[CH2:18][CH:19]=[CH:20][C@H:13]12)[CH:32]=[CH2:31]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 2733832Lithium HexamethyldisilazideHCID 9838161HCID 9838161, compound

Product 1

HCID 70087875HCID 70087875, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Analogously to the procedure of Example 3, the title compound was prepared from 0.79 g (3 mmol) of the compound from Example 7, 3 ml of 1 molar lithium bis(trimethylsilyl)-amide solution in THF and 0.36 g (3 mmol) of allyl bromide in 10 ml of THF. Chromatographic purification was carried out using a mixture of dichloromethane and petroleum ether (40-60) in a ratio of 100:4. Yield: 684 mg (74.8%) of a pale yellow oil; Diastereomeric purity: >99% de (HPLC). MS (DCI/NH3) [m/e]: 322 (100, M+NH4+) 1H-NMR (200 MHz; CDCl3): δ[ppm]=2.24 (dd,1H); 2.37 (dd,1H), 2.72 (m,2H), 3.16 (d,1H), 3.28 (d,1H), 3.48(m,1H), 5.03 (dd,1H), 5.05 (m,1H), 5.12 (dd,1H), 5.78 (ddt,1H), 5.89 (m,1H), 6.04 (m,1H), 7.4-7.5 (br m,3H), 7.75 (s,1H), 7.8 (m,3H)

Workup

  1. customChromatographic purification
  2. additiona mixture of dichloromethane and petroleum ether (40-60) in a ratio of 100:4

Sources & evidence

ORD record
ord-a037d71117634b41a07e6604125c82c7
Source dataset
uspto-grants-2002_08
Patent number
US06433004B1

Reaction notes

Loading…