Carbon tetrabromide → (S,E)-tert-butyl 2-(4-(bromomethyl)styryl)pyrrolidine-1-carboxylate

HRID 923446Notes

Reaction equation

HRID 923446 reaction equation
O[CH2:2][C:3]1[CH:22]=[CH:21][C:6](/[CH:7]=[CH:8]/[C@@H:9]2[CH2:13][CH2:12][CH2:11][N:10]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:43]>C1COCC1>[Br:43][CH2:2][C:3]1[CH:22]=[CH:21][C:6](/[CH:7]=[CH:8]/[C@@H:9]2[CH2:13][CH2:12][CH2:11][N:10]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66749853(S,E)-tert-butyl 2-(4-(hydroxymethyl)styryl)pyrrolidine-1-carboxylate

Product 1

HCID 68765291(S,E)-tert-butyl 2-(4-(bromomethyl)styryl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Example 149C (0.9 g, 2.97 mmol) dissolved in THF (50 mL) was added resin bound triphenylphosphine (5.93 mmol) and carbon tetrabromide (1.48 g, 4.45 mmol) and the resultant solution stirred at room temperature for 2 hours. The resin was then filtered off, washed with THF and the combined filtrate was then dried, filtered, and concentrated to afford the title compound. m/z 368 (M+H)+.

Workup

  1. additionwas added resin
  2. filtrationThe resin was then filtered off
  3. washwashed with THF
  4. customthe combined filtrate was then dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d6438d330b3547df91fccf157de3e368
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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