Allyl bromide → HCID 86749014, compound

HRID 1198490Notes

Reaction equation

HRID 1198490 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15]N2CCCC2=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Li+].C[CH:24]([N-:26][CH:27]([CH3:29])C)[CH3:25].[CH2:30](Br)[CH:31]=[CH2:32].C1C[O:37]CC1>>[C:1]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH:32]=[C:31]([CH:29]2[CH2:25][CH2:24][NH:26][C:27]2=[O:37])[CH3:30])[CH2:12][CH2:13]1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 4

HCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 2724682Lithium diisopropylamideHCID 19380957HCID 19380957, compound

Product 1

HCID 86749014HCID 86749014, compoundYield 45%

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 19(325 mg, 1.1 mmol) in THF (5 mL) at -78° C. was added LDA (0.5M in THF 2.4 mL) dropwise. After 15 min allyl bromide (0.16 mL, 2.2 mmol) was added and the reaction stirred at -78° C. for 1 hr followed by quenching with HOAc (0.1 mL). The reaction mixture was then diluted with ethyl acetate and then washed with water and brine, dried (MgSO4), and concentrated. Flash chromatography (silica gel, 50% ethyl acetate/hexanes) gave 20 (160 mg, 45%) as an oil. TLC Rf-0.23 (50% ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 5.80 (m, 1H), 5.10 (m, 2H), 4.10 (m, 2H), 3.32 (m, 4H), 2.70 (m, 2H), 2.56 (m, 2H), 2.20 (m, 2 H), 1.73 (m, 3H), 1.48 (s, 9H), 1.13 (m, 2H) .

Workup

  1. customby quenching with HOAc (0.1 mL)
  2. additionThe reaction mixture was then diluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2fc1ddb364a34a219077742365cb5111
Source dataset
uspto-grants-1994_01
Patent number
US05281585

Reaction notes

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