Acetic Acid → HCID 178484112, compound

HRID 2271565Notes

Reaction equation

HRID 2271565 reaction equation
N[C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.C=O.[C:18]([BH3-])#[N:19].[Na+].[C:22](O)(=O)C>CO>[CH3:22][N:19]([CH3:18])[C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178419079HCID 178419079, compound

Product 1

HCID 178484112HCID 178484112, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl trans-4-aminocyclohexylcarbamate (750 mg, 3.50 mmol), paraformaldehyde (318 mg, 10.5 mmol), and sodium cyanoborohydride (660 mg, 13.5 mmol) in methanol (30 mL) was added acetic acid (catalytic) and the reaction stirred at room temperature for 18 h. The reaction mixture was quenched with water and the layers were separated. The pH of the aqueous layer was adjusted to 10 using 1 M sodium hydroxide followed by extraction with methylene chloride. The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to afford the desired product (805 mg, 95%) as a white solid: ESI MS m/z 243 [C13H26N2O2+H]+.

Workup

  1. customThe reaction mixture was quenched with water
  2. customthe layers were separated
  3. extractionfollowed by extraction with methylene chloride
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cd8095430864473880d061676b5033f6
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

Loading…