Formaldehyde → HCID 89648817, compound

HRID 2207675Notes

Reaction equation

HRID 2207675 reaction equation
Cl.[CH3:2][N:3]1[CH2:27][CH2:26][C@:5]2([NH:9][C@@H:8]([C:10]3[CH:15]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=4)[CH:13]=[CH:12][N:11]=3)[CH2:7][CH2:6]2)[C:4]1=[O:28].C=O.[C:31](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:31][N:9]1[C@:5]2([CH2:26][CH2:27][N:3]([CH3:2])[C:4]2=[O:28])[CH2:6][CH2:7][C@@H:8]1[C:10]1[CH:15]=[C:14]([C:16]2[CH:17]=[CH:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=2)[CH:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 89649733HCID 89649733, compound

Product 1

HCID 89648817HCID 89648817, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2R,5S)-7-methyl-2-[4-[4-(trifluoromethyl)phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride (which may be prepared as described in Example 52) (21 mg, 0.0500 mmol) in methanol (0.5000 mL) was added 3 meq of 3.7% formalin solution and sodium triacetoxyborohydride (16.21 mg, 0.0800 mmol) and the mixture was stirred for 1 h. The mixture was evaporated and partitioned between satd. aq. NaHCO3 (2 ml) and MDC (3×5 ml) and the residue purified on an SCX-2 cartridge (0.5 g) eluting with MeOH to 2% aq NH3 in MeOH to give (2R,5S)-1,7-dimethyl-2-[4-[4-(trifluoromethyl)phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]nonan-6-one, a clear oil (16.9 mg);

Workup

  1. customThe mixture was evaporated
  2. custompartitioned between satd
  3. customaq. NaHCO3 (2 ml) and MDC (3×5 ml) and the residue purified on an SCX-2 cartridge (0.5 g)
  4. washeluting with MeOH to 2% aq NH3 in MeOH

Sources & evidence

ORD record
ord-60616a9d03d9469bb9d89459300e7956
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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