Dichloromethane → HCID 71643944, compound

HRID 252129Notes

Reaction equation

HRID 252129 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[N:14]=2)[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O.[Cl:28]CCl>>[ClH:28].[Br:19][C:15]1[N:14]=[C:13]([N:10]2[CH2:11][CH2:12][C@H:8]([NH2:7])[CH2:9]2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 71629158HCID 71629158, compound

Product 1

HCID 71643944HCID 71643944, compoundYield 88%

Procedure

Combine (3S)-[1-(6-bromopyridin-2-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (260 mg, 0.76 mmol) and dichloromethane (10 mL). Add trifluoroacetic acid (2 mL) and stir at room temperature for 4 hours. Concentrate and dissolve in methanol. Load onto Dowex® 1×2-200 column and elute with methanol. Concentrate and add acetone to give a solid. Filter the solid to give (3S)-1-(6-bromopyridin-2-yl)-pyrrolidin-3-ylamine hydrochloride (187 mg, 88%). 1H NMR (400 MHz, MeOH-d4) δ 7.39 (t, 1H, J=7.6 Hz), 6.77 (d, 1H, J=7.6 Hz), 6.47 (d, 1H, J=7.6 Hz), 4.04-3.99 (m, 1H), 3.80-3.75 (m, 1H), 3.66-3.59 (m, 2H), 3.56-3.50 (m, 1H), 2.52-2.43 (m, 1H), 2.21-2.13 (m, 1H).

Workup

  1. concentrationConcentrate
  2. dissolutiondissolve in methanol
  3. washLoad onto Dowex® 1×2-200 column and elute with methanol
  4. concentrationConcentrate
  5. additionadd acetone
  6. customto give a solid
  7. filtrationFilter the solid

Sources & evidence

ORD record
ord-b7ca6bd2dd54465892dc7d6794541885
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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