Dichloromethane → HCID 67570491, compound

HRID 611594Notes

Reaction equation

HRID 611594 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]2[O:17][C:16]([C@H:18]3[CH2:22][CH2:21][CH2:20][N:19]3C(OC(C)(C)C)=O)=[CH:15][C:12]2=[N:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:38]>>[ClH:38].[C:1]([C:9]1[CH:10]=[C:11]2[O:17][C:16]([C@H:18]3[CH2:22][CH2:21][CH2:20][NH:19]3)=[CH:15][C:12]2=[N:13][CH:14]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 18396243HCID 18396243, compound

Product 1

HCID 67570491HCID 67570491, compound

Conditions

Temperature
0 °C

Procedure

6-(benzoyl)-2-(1-Boc-2-(R)-pyrrolidinyl)furo[3,2-b]pyridine is dissolved in CH2Cl2 (10 mL). The mixture is cooled to 0° C., TFA (10 mL) is added and the reaction is stirred for 45 minutes as it warms to room temperature. The mixture is concentrated in vacuo and taken up in a minimum amount of H2O. The aqueous mixture is basified with 15% NaOH and extracted with CH2Cl2 (200 mL), which is dried (MgSO4) and concentrated. The residue is chromatographed (silica gel) to afford the free amine. The isolated free amine is taken up in a minimum amount of Et2O, cooled to 0° C., and treated with HCl in EtOH to afford the hydrochloride salt.

Workup

  1. customwarms to room temperature
  2. concentrationThe mixture is concentrated in vacuo
  3. extractionextracted with CH2Cl2 (200 mL), which
  4. dry with materialis dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue is chromatographed (silica gel)

Sources & evidence

ORD record
ord-4f69ef35efbb43ce8476c4009793723b
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

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