Hydrochloric Acid → HCID 70208604, compound

HRID 611590Notes

Reaction equation

HRID 611590 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[O:21][C:20]2[C:15](=[N:16][CH:17]=[CH:18][C:19]=2[Cl:22])[CH:14]=1)(OC(C)(C)C)=O.Cl>C(O)=O>[ClH:22].[Cl:22][C:19]1[CH:18]=[CH:17][N:16]=[C:15]2[CH:14]=[C:13]([C@@H:9]3[CH2:10][CH2:11][CH2:12][N:8]3[CH3:1])[O:21][C:20]=12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18396233HCID 18396233, compound

Product 1

HCID 70208604HCID 70208604, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 2-(1-BOC-2-(S)-pyrrolidinyl)-7-chlorofuro[3,2-b]pyridine, from step 51a above, in HCO2H (15.0 mL, 88%) and H2CO (15 mL, 37%) was refluxed for one hour. After cooling to room temperature and the solution was acidified to pH=2.0 with 1 N aqueous HCl and washed with Et2O (150 mL). The aqueous layer was basified with 15% NaOH and extracted with CH2Cl2 (4×400 mL). The combined CH2Cl2 extracts were dried (MgSO4) and concentrated. The crude material was chromatographed (silica gel; CH2Cl2 :MeOH, 95:5) to afford the title compound as a light yellow oil (0.036 g, 15%). The amine was dissolved in Et2O and cooled to 0° C. and a saturated solution of HCl in Et2O was added until precipitation ceased. The solvent was removed and the yellow solid was placed under vacuum to afford the title compound: [α]D≤ +26.24 (c 0.05, H2O); 1H NMR (D2O, 300 MHz) δ 2.28-2.42 (m, 2H), 2.50-2.68 (m, 2H), 2.98 (s, 3H), 3.42 (br s, 1H), 3.62 (br s, 1H), 5.00 (m, 1H), 7.38 (s, 1H), 7.59 (d, J=6.0 Hz, 1H), 8.44 (d, J=6.0 Hz, 1H); MS (DCI/NH3) m/z: 237 (M+H)+ ; Anal. Calcd for C12H13N2O.1.2 HCl.0.10H2O.0.20Et2O: C, 51.75; H, 5.56; N, 9.43. Found C, 51.40; H, 5.49; N,9.03.

Workup

  1. washwashed with Et2O (150 mL)
  2. extractionextracted with CH2Cl2 (4×400 mL)
  3. dry with materialThe combined CH2Cl2 extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude material was chromatographed (silica gel; CH2Cl2 :MeOH, 95:5)

Sources & evidence

ORD record
ord-4de781db63cf4921b6bbb16e682d808d
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

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