Allyl bromide → HCID 66853728, compound

HRID 862237Notes

Reaction equation

HRID 862237 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C@H:14]([OH:15])[CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:19](Br)[CH:20]=[CH2:21]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:16][C@H:14]([O:15][CH2:21][CH:20]=[CH2:19])[CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Product 1

HCID 66853728HCID 66853728, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-tert-Butoxycarbonyl (4R)-hydroxyproline (9.25 g, 40 mmol) was added to a solution of 60% sodium hydride (3.36 g, 84 mmol) in 100 ml of anhydrous tetrahydrofuran and stirred for 2 hours at room temperature. Allyl bromide (6.9 ml, 80 mmol) was added to the mixture and refluxed for 6 hours. The mixture was quenched with the addition of ice chips, then additional water was added and the mixture was washed with hexane. The aqueous layer was acidified with 10% sodium hydrogen sulfate and extracted with ethyl acetate (2×150 ml). The combined extracts were dried over anhydrous sodium sulfate, filtered and evaporated to give 5 g of the title product with no further purification. 1NMR (CDCl3 ; exist as rotamers) δ 5.92-5.82 (1H, m), 5.3-5.14 (2H, m) 4.5-4.31 (1H, m), 4.16-4.05 (1H, m), 4.04-3.9 (1H, m), 3.79-3.5 (3H, m), 2.43-2.2 (1.5H, m), 2.15-2.10 (0.5H, m), 1.45 (4.5H, s), 1.35 (4.5H, s).

Workup

  1. temperaturerefluxed for 6 hours
  2. customThe mixture was quenched with the addition of ice chips
  3. additionadditional water was added
  4. washthe mixture was washed with hexane
  5. extractionextracted with ethyl acetate (2×150 ml)
  6. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-c7379b2c7b25402bacf2243ec8f84586
Source dataset
uspto-grants-1998_02
Patent number
US05716929

Reaction notes

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