Formaldehyde → HCID 178500694, compound

HRID 491829Notes

Reaction equation

HRID 491829 reaction equation
Cl.N[C@H]1C[CH2:7][C@H:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:5][CH2:4]1.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+].[CH2:35]([N:37]([CH2:40]C)[CH2:38][CH3:39])C>ClCCl>[CH3:40][N:37]([CH3:35])[C@H:38]1[CH2:39][CH2:7][C@H:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:5][CH2:4]1

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 178500693HCID 178500693, compound

Product 1

HCID 178500694HCID 178500694, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under ice-cooling, to a suspension of methyl trans-(4-aminocyclohexyl)acetate hydrochloride (895 mg) obtained in Reference Example 120(4) in dichloromethane (30 ml), triethylamine (1.2 ml) is added and the mixture is stirred. Aqueous 35% formaldehyde solution (1.71 ml) and sodium triacetoxy borohydride (2.74 g) are added thereto successively under ice-cooling. The reaction solution is warmed to room temperature and stirred for 6 hours. Saturated aqueous sodium hydrogen carbonate solution is poured into the mixture under ice-cooling and the mixture is extracted with chloroform. The organic layer is washed with saturated brine, dried over sodium sulfate, and then the solvent is removed under reduced pressure to give methyl trans-[4-(dimethylamino)cyclohexyl]acetate (771 mg).

Workup

  1. temperaturesuccessively under ice-cooling
  2. stirringstirred for 6 hours
  3. temperaturecooling
  4. extractionthe mixture is extracted with chloroform
  5. washThe organic layer is washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-e21bd735443e4cacb6eee8ace79e6433
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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