Acetic Acid → HCID 178484043, compound

HRID 2271567Notes

Reaction equation

HRID 2271567 reaction equation
N[C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4][CH2:3]1.C=O.[C:19]([BH3-])#[N:20].[Na+].[C:23](O)(=O)C>CO>[CH3:23][N:20]([CH3:19])[C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178453642HCID 178453642, compound

Product 1

HCID 178484043HCID 178484043, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl [trans-4-aminocyclohexyl]methylcarbamate (1.15 g, 5.00 mmol), paraformaldehyde (454 mg, 15.0 mmol), and sodium cyanoborohydride (940 mg, 15.0 mmol) in methanol (40 mL) was added acetic acid (catalytic) and the reaction mixture stirred at room temperature for 18 h. The reaction mixture was quenched with water and concentrated to remove methanol. The pH of the aqueous layer was adjusted to 10 with 1 M aqueous sodium hydroxide followed by extraction with methylene chloride. The organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to afford the desired product (1.23 g, 96%) as a thick oil: ESI MS m/z 257 [C14H28H2O2+H]+.

Workup

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

Sources & evidence

ORD record
ord-4239f9fb15304b7ea5dc3283d2257560
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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