Acetic Acid → HCID 86681543, compound

HRID 709010Notes

Reaction equation

HRID 709010 reaction equation
[CH3:1][C:2]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[C:3]=1[C:4]([O:6][CH:7]([CH3:23])[CH2:8][N:9]([C:16](OC(C)(C)C)=O)[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:5].C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>Cl.O1CCOCC1.C(Cl)Cl>[CH3:1][C:2]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[C:3]=1[C:4]([O:6][CH:7]([CH3:23])[CH2:8][N:9]([CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[CH3:16])=[O:5]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86681541HCID 86681541, compound

Product 1

HCID 86681543HCID 86681543, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

1-((tert-butoxycarbonyl)(cyclohexyl)amino)propan-2-yl 2,4,6-trimethyl-benzoate (1.0 g, 2.48 mmol) was dissolved in dioxane-HCl (15 mL). The reaction mixture was stirred at rt for 2 hours. Solvent was evaporated. Crude solid was dissolved in DCE (10 ml) and formaldehyde (0.34 mL, 3.96 mmol), and sodium triacetoxyborohydride (1.67 g, 7.92 mmol) and acetic acid (0.5 mL) were added at 0° C. The resultant reaction mixture was stirred at rt for 16 hours. The reaction mixture was diluted in DCM and washed with 1N NaOH, water and brine. The organic layer was dried over sodium sulphate and concentrated to dryness. The crude compound was purified by column chromatography to obtain 1-(cyclohexyl(methyl)amino)propan-2-yl 2,4,6-trimethylbenzoate. Yield: 0.6 (76%); 1H NMR (400 MHz, CDCl3) δ 6.82 (s, 2H), 5.27-5.25 (m, 1H), 2.64-2.62 (m, 1H), 2.51-2.46 (m, 1H), 2.29 (s, 9H), 2.25 (s, 3H), 1.75-1.74 (m, 4H), 1.33-1.31 (d, J=6 Hz, 3H), 1.18-1.13 (m, 4H), 1.09-1.03 (m, 1H); LCMS: m/z=317.8 [M+H], RT=2.98 min (Column: X, Program: P1).

Workup

  1. customSolvent was evaporated
  2. dissolutionCrude solid was dissolved in DCE (10 ml)
  3. customThe resultant reaction mixture
  4. stirringwas stirred at rt for 16 hours
  5. washwashed with 1N NaOH, water and brine
  6. dry with materialThe organic layer was dried over sodium sulphate
  7. concentrationconcentrated to dryness
  8. customThe crude compound was purified by column chromatography

Sources & evidence

ORD record
ord-d4fee0845fd849ccb6c12ba904eb9b73
Source dataset
uspto-grants-2015_11
Patent number
US09180115B2

Reaction notes

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