4-Bromophenacyl bromide → (S)-tert-butyl 2-(4-(4-bromophenyl)thiazol-2-yl)pyrrolidine-1-carboxylate

HRID 1963974Notes

Reaction equation

HRID 1963974 reaction equation
[C:1]([C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(=[S:3])[NH2:2].[Br:16][C:17]1[CH:26]=[CH:25][C:20]([C:21](=O)[CH2:22]Br)=[CH:19][CH:18]=1>C(O)C>[Br:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]2[N:2]=[C:1]([C@@H:4]3[CH2:8][CH2:7][CH2:6][N:5]3[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[S:3][CH:22]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 74544-Bromophenacyl bromideHCID 54006182tert-Butyl (2S)-2-carbamothioylpyrrolidine-1-carboxylate2×

Product 1

HCID 67224730(S)-tert-butyl 2-(4-(4-bromophenyl)thiazol-2-yl)pyrrolidine-1-carboxylateYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (S)-tert-butyl 2-carbamothioylpyrrolidine-1-carboxylate (compound 11a, 2.2 g, 9.6 mmol) and 4-bromophenacyl bromide (2.9 g, 10.5 mmol) in ethanol (50 ml) was stirred at room temperature for 3 hours. The resulting mixture was extracted with ethyl acetate and the organic layer was dried over MgSO4, filtered and concentrated to give crude product. The crude product was purified with column chromatography (ethyl acetate:n-hexane=1:3) to yield pure product 12a (3.3 g).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude product
  6. customThe crude product was purified with column chromatography (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-9ccbd8255ae3420091152a5f616b44f0
Source dataset
uspto-grants-2013_04
Patent number
US08415482B2

Reaction notes

Loading…