Ethyl Bromide → HCID 12709313, compound

HRID 1697553Notes

Reaction equation

HRID 1697553 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:17](Br)[CH3:18]>C(OCC)(=O)C>[CH3:17][CH2:18][O:15][C:14]([C@@H:9]1[CH2:10][C@H:11]([OH:13])[CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:16]

Participants

4

Reactant 2

HCID 6332Ethyl BromideHCID 688614(2S,4S)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Product 1

HCID 12709313HCID 12709313, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (2S,4S)-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (1.0 eq, 5.0 g) in ethyl acetate (250 mL) was added dicyclohexamine (2.0 eq, 8.62 mL) and the reaction stirred for 5 mins during which time a white precipitate formed. Part of the ethyl acetate was evaporated and the slurry left to stand for 30 mins, then filtered and washed with diethyl ether (30 mL). The filtrate was dried briefly under high vacuum and then resuspended in anhydrous DMF (50 mL). The reaction mixture was then treated with ethyl bromide (4.0 eq, 6.46 mL) and stirred in a sealed flask for 18 hours. TLC and MS revealed that the reaction was complete. The reaction mixture was filtered and washed with ethyl acetate (2×20 mL). The filtrate was then evaporated to dryness, the residue taken up in ethyl acetate (50 mL) and the organic layer washed once with water and once with brine, dried over sodium sulfate, filtered and evaporated to yield a colourless oil (4.87 g; 87%). The crude product was used without further purification. MS (ESI): m/z=204.1 [M+H-Boc]+.

Workup

  1. customformed
  2. customPart of the ethyl acetate was evaporated
  3. waitthe slurry left
  4. waitto stand for 30 mins
  5. filtrationfiltered
  6. washwashed with diethyl ether (30 mL)
  7. customThe filtrate was dried briefly under high vacuum
  8. stirringstirred in a sealed flask for 18 hours
  9. filtrationThe reaction mixture was filtered
  10. washwashed with ethyl acetate (2×20 mL)
  11. customThe filtrate was then evaporated to dryness
  12. washthe organic layer washed once with water and once with brine
  13. dry with materialdried over sodium sulfate
  14. filtrationfiltered
  15. customevaporated
  16. customto yield a colourless oil (4.87 g; 87%)
  17. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-9cc7096ffc4449f48b5ecd95dab395a8
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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