Formaldehyde → HCID 21309669, compound

HRID 617338Notes

Reaction equation

HRID 617338 reaction equation
[NH:1]1[CH2:4][CH2:3][C@H:2]1[CH2:5][O:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([Br:13])[CH:12]=1.C=O.[BH3-][C:17]#N.[Na+]>C(O)(=O)C>[CH3:17][N:1]1[CH2:4][CH2:3][C@H:2]1[CH2:5][O:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([Br:13])[CH:12]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 10421874HCID 10421874, compound

Product 1

HCID 21309669HCID 21309669, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 480 mg sample of the free base of 3-(2-(S)-azetidinylmethoxy)-5-bromopyridine, from Example 67 above, was dissolved in 4 mL of acetic acid treated with 1 mL of 37% HCHO and 500 mg of NaBH3CN at 0° C. for 4 hr. The solvents were removed under reduced pressure. The residue was basified with NaHCO3 solution. The mixture was extracted with methylene chloride, the extract was dried over MgSO4, and the solvent was removed. The residue was purified by chromatography on silica gel, eluting with 200:1 and 100:1 chloroform:methanol to give 68 mg of the title compound. MS (DCI/NH3) m/e: 257/259 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.28 (d, J=1.9 Hz, 1H), 8.26 (d, J=2.6 Hz, 1H), 7.38 (dd, J=1.9, 2.6 Hz, 1H), 4.02 (d, J=6.3 Hz, 2H), 3.51-3.44 (m, 1H), 3.43-3.37 (m, 1H), 2.93-2.84 (m, 1H), 2.41 (s, 3H), 2.13-2.03 (m, 2H).

Workup

  1. customThe solvents were removed under reduced pressure
  2. extractionThe mixture was extracted with methylene chloride
  3. dry with materialthe extract was dried over MgSO4
  4. customthe solvent was removed
  5. customThe residue was purified by chromatography on silica gel
  6. washeluting with 200:1 and 100:1 chloroform

Sources & evidence

ORD record
ord-3e74bacfc36e46c7a978b331856ef188
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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