Hydrogen Bromide → (9H-fluoren-9-yl)methyl 4-(bromoacetyl)piperidine-1-carboxylate

HRID 522862Notes

Reaction equation

HRID 522862 reaction equation
[N+](=[CH:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][CH:16]2[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:22]3[C:17]2=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:13])[CH2:8][CH2:7]1)=[O:5])=[N-].[BrH:29]>C1COCC1.O>[Br:29][CH2:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][CH:16]2[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:22]3[C:17]2=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:13])[CH2:8][CH2:7]1)=[O:5]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 866474499H-fluoren-9-ylmethyl-4-(diazoacetyl)piperidine-1-carboxylate

Product 1

HCID 86685241(9H-fluoren-9-yl)methyl 4-(bromoacetyl)piperidine-1-carboxylateYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (9H-fluoren-9-yl)methyl 4-(diazoacetyl)piperidine-1-carboxylate (5 g, 13.3 mmol) in THF was cooled in an ice water bath and was treated with an aqueous HBr solution (10 mL). This reaction mixture was stirred at RT for 2 h. The reaction mixture was diluted with water and the organic content was extracted using EtOAc, dried over Na2SO4, filtered and concentrated at reduced pressure. The crude product was chromatographed over silica gel eluting with a gradient (0-15% EtOAc:hexanes) to afford (9H-fluoren-9-yl)methyl 4-(bromoacetyl)piperidine-1-carboxylate (3 g, 53%) as an off white solid.

Workup

  1. extractionthe organic content was extracted
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure
  5. customThe crude product was chromatographed over silica gel eluting with a gradient (0-15% EtOAc:hexanes)

Sources & evidence

ORD record
ord-df99140cba08482bb3c56295135abb14
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

Loading…