Dichloromethane → HCID 66856299, compound

HRID 252118Notes

Reaction equation

HRID 252118 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C@H:15]1[CH2:19][CH2:18][N:17]([C:20]2[N:25]=[CH:24][C:23]([Br:26])=[CH:22][N:21]=2)[CH2:16]1)(C)(C)C.[Cl:28]CCl>>[ClH:28].[Br:26][C:23]1[CH:22]=[N:21][C:20]([N:17]2[CH2:18][CH2:19][C@H:15]([NH2:14])[CH2:16]2)=[N:25][CH:24]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66854295HCID 66854295, compound

Product 1

HCID 66856299HCID 66856299, compoundYield 85%

Procedure

Add trifluoroacetic acid (20 mL) to a solution of (S)-[1-(5-bromopyrimidin-2-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (3.66 g, 10.7 mmol) in dichloromethane (20 mL). Stir 2 h and concentrate. Dissolve the residue in methanol and pass through a column of Amberjet® 4400 resin (OH-form). Wash the column with methanol and concentrate the eluant. Dissolve the residue in methanol/acetonitrile and add 1 N HCl (25 mL) in methanol. Collect the resulting solid by filtration, wash with acetonitrile and dry the solid to give (S)-1-(5-bromopyrimidin-2-yl)-pyrrolidin-3-ylamine hydrochloride as a tan solid (2.55 g, 85%).

Workup

  1. concentrationconcentrate
  2. dissolutionDissolve the residue in methanol
  3. washWash the column with methanol
  4. concentrationconcentrate the eluant
  5. dissolutionDissolve the residue in methanol/acetonitrile
  6. additionadd 1 N HCl (25 mL) in methanol
  7. customCollect the resulting solid
  8. filtrationby filtration
  9. washwash with acetonitrile
  10. customdry the solid

Sources & evidence

ORD record
ord-d8f2ec77a2a643cb8bcdfb97ab2d863d
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

Loading…