Dichloromethane → HCID 70204345, compound

HRID 611566Notes

Reaction equation

HRID 611566 reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[O:21][C:16]2=[CH:17][N:18]=[CH:19][CH:20]=[C:15]2[CH:14]=1)(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+].C(Cl)[Cl:36]>>[ClH:36].[ClH:36].[NH:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[O:21][C:16]2=[CH:17][N:18]=[CH:19][CH:20]=[C:15]2[CH:14]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 183962351,1-Dimethylethyl (2S)-2-furo[2,3-c]pyridin-2-yl-1-pyrrolidinecarboxylate

Product 1

HCID 70204345HCID 70204345, compound

Conditions

Temperature
0 °C

Procedure

To a 700 mg sample of the compound from step 9c above in 5 mL of CH2Cl2 at 0° C. was added 5 mL of TFA. The reaction mixture was stirred for 1 hour at 0° C. then poured into saturated Na2CO3, and the layers were separated. The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated, and the residue was chromatographed on silica gel, eluting with 100:0 to 95:5 CHCl3 :MeOH. The product was converted to the salt by treatment with HCl/ether, which was recrystallized from ethanol/EtOAc: 1H NMR (D2O, 300 MHz) δ 2.19-2.52 (m, 3H), 2.64 (m, 1H), 3.53-3.58 (m, 2H), 5.13 (t, 1H, J=8 Hz), 7.34 (s, 1H), 8.05 (dd, 1H, J=0.8, 5.8 Hz), 8.49 (d, 1H, J=5.8 Hz), 9.07 (s, 1H); MS m/z: 189 (M+H)+, 206 (M+NH4)+ ; Anal. Calcd for C11H12N2O·2.0 HCl.H2O: C, 47.33; H, 5.78; N, 10.03. Found: C, 47.32; H, 5.83; N, 9.90.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customthe residue was chromatographed on silica gel
  6. washeluting with 100:0 to 95:5 CHCl3
  7. customwas recrystallized from ethanol/EtOAc

Sources & evidence

ORD record
ord-3e37cc1092df48c2a81c359c4e79451e
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

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