Formaldehyde → HCID 178483491, compound

HRID 2178885Notes

Reaction equation

HRID 2178885 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15]N)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH2:18]=O.[C:20]([BH3-])#[N:21].[Na+]>CO.C(O)(=O)C.C([O-])(O)=O.[Na+]>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][N:21]([CH3:20])[CH3:18])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178453920HCID 178453920, compound

Product 1

HCID 178483491HCID 178483491, compoundYield 31.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a suspension of tert-butyl[trans-4-(2-aminoethyl)cyclohexyl]carbamate (970 mg, 4.0 mmol) and paraformaldehyde (360 mg, 12 mmol) in methanol (40 mL) was added sodium cyanoborohydride (750 mg, 12 mmol) and acetic acid (1 drop). The resultant suspension was stirred at room temperature for 16 h, diluted with a saturated NaHCO3 solution and extracted with a mixture of CHCl3/isopropanol (3:1). The combined organic layers were dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, methanol/dichloromethane) to afford the desired product (340 mg, 31%) as a white solid. ESI MS m/z 271 [C15H30N2O2+H]+

Workup

  1. extractionextracted with a mixture of CHCl3/isopropanol (3:1)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography (silica, methanol/dichloromethane)

Sources & evidence

ORD record
ord-959802e13e654a529a18f9e1454232a7
Source dataset
uspto-grants-2015_06
Patent number
US09067937B2

Reaction notes

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