Dichloromethane → (S)-1-(6-fluoropyridin-3-yl)-pyrrolidin-3-ylamine hydrochloride

HRID 252107Notes

Reaction equation

HRID 252107 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH:15]1[CH2:19][CH2:18][N:17]([C:20]2[CH:21]=[N:22][C:23]([F:26])=[CH:24][CH:25]=2)[CH2:16]1)(C)(C)C.[Cl:28]CCl>>[ClH:28].[F:26][C:23]1[N:22]=[CH:21][C:20]([N:17]2[CH2:18][CH2:19][C@H:15]([NH2:14])[CH2:16]2)=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66854924[1-(6-Fluoropyridin-3-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 66854645(S)-1-(6-fluoropyridin-3-yl)-pyrrolidin-3-ylamine hydrochlorideYield 70%

Procedure

Add trifluoroacetic acid (5 mL) to a solution of [1-(6-fluoropyridin-3-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (840 mg, 3.0 mmol) in dichloromethane (5 mL). Stir for 1 h then concentrate to dryness. Dissolve the residue in methanol and pass through a column of Dowex® 1x2-200 (Cl− form). Concentrate the residue and crystallize from methanol and acetone to give (S)-1-(6-fluoropyridin-3-yl)-pyrrolidin-3-ylamine hydrochloride as a tan solid (453 mg, 70%).

Workup

  1. concentrationthen concentrate to dryness
  2. dissolutionDissolve the residue in methanol
  3. concentrationConcentrate the residue
  4. customcrystallize from methanol and acetone

Sources & evidence

ORD record
ord-c6566983c84d44699d73a1890bc7a62e
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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