Hydrochloric Acid → HCID 22857705, compound

HRID 2259198Notes

Reaction equation

HRID 2259198 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=1)(OC(C)(C)C)=O.C=O.[ClH:25]>C(O)=O>[ClH:25].[F:22][C:17]1[CH:16]=[C:15]([CH:20]=[C:19]([F:21])[CH:18]=1)[O:14][CH2:13][C@@H:9]1[CH2:10][CH2:11][CH2:12][N:8]1[CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 22857711HCID 22857711, compound

Product 1

HCID 22857705HCID 22857705, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A 0.25 g (0.8 mmol) sample of (S)-N-BOC-2-(3,5-difluorophenoxymethyl)pyrrolidine, from Example 7b above, was dissolved in 10 mL of a 2:1 mixture of formic acid:formaldehyde and stirred for 16 hr at reflux. To this solution was added excess 10% HCl, and the mixture was extracted twice with ethyl acetate. The aqueous layer was adjusted to pH 12 with K2CO3 and then extracted with methylene chloride. The solvent was dried over MgSO4 and removed under vacuum to yield the crude product, which was then triturated with ether as ethanolic HCl was added. Repeated drying and washing with ether gave 0.118 g of title product. MS: 228 (M+H)+. NMR (D2O) δ: 2.01-2.24 (m, 2H), 2.34-2.43 (m, 1H), 3.02 (s, 3H), 3.27 (br s, 1H), 3,78 (br s, 1H), 3.92 (br s, 1H), 4.27 (dd, 1H, J=6, 11 Hz), 4.44 (dd, 1H, J=3, 11 Hz), 6.63-6.71 (m, 3H). Anal. Calcd for C12H16ClF2NO.0.8 H2O: C, 51.82; H, 6.38; N, 5.04; Found: C, 51.77; H, 6.06; N, 4.82.

Workup

  1. temperatureat reflux
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. extractionextracted with methylene chloride
  4. dry with materialThe solvent was dried over MgSO4
  5. customremoved under vacuum
  6. customto yield the crude product, which
  7. customwas then triturated with ether as ethanolic HCl
  8. additionwas added
  9. customRepeated drying
  10. washwashing with ether

Sources & evidence

ORD record
ord-0d76e23ce7cb4f359a39f6b88bdfc277
Source dataset
uspto-grants-1995_12
Patent number
US05472958

Reaction notes

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