Formaldehyde → HCID 178483491, compound

HRID 2271537Notes

Reaction equation

HRID 2271537 reaction equation
N[CH2:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][CH2:5]1.[CH2:18]=O.[C:20]([BH3-])#[N:21].[Na+]>CO.C(O)(=O)C.C([O-])(O)=O.[Na+]>[CH3:18][N:21]([CH3:20])[CH2:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][CH2:5]1

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178453920HCID 178453920, compound

Product 1

HCID 178483491HCID 178483491, compoundYield 31.1%

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 mmol) and paraformaldehyde (360 mg, 12 mmol) in methanol (40 mL) was added sodium cyanoborohydride (754 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 and concentrated. Purification by column chromatography (silica, 0-20% methanol/dichloromethane) afforded the desired product (336 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. concentrationconcentrated
  4. customPurification by column chromatography (silica, 0-20% methanol/dichloromethane)

Sources & evidence

ORD record
ord-32f3accd48774fc58d8d88595df099fb
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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