Acetic Acid → HCID 178484112, compound

HRID 2178890Notes

Reaction equation

HRID 2178890 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.O.C(Cl)Cl>[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

8

Reactant 4

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

Product 1

HCID 178484112HCID 178484112, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl trans-4-aminocyclohexylcarbamate (750 mg, 3.5 mmol), paraformaldehyde (320 mg, 10 mmol), and sodium cyanoborohydride (660 mg, 13 mmol) in methanol (30 mL) was added acetic acid (catalytic) and the reaction was stirred at room temperature for 18 h. The reaction mixture was diluted with water and methylene chloride the layers were separated. The aqueous layer was adjusted to pH 10 using 1 M sodium hydroxide followed by extraction with methylene chloride. The combined organic layers were dried over sodium sulfate, filtered and the filtrate was concentrated to afford the desired product (800 mg, 95%) as a white solid: ESI MS m/z 243 [C13H26N2O2+H]+.

Workup

  1. customwere separated
  2. extractionfollowed by extraction with methylene chloride
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d1b3c2f1897a4604856e539982ac71d9
Source dataset
uspto-grants-2015_06
Patent number
US09067937B2

Reaction notes

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