Acetic Acid → HCID 178464369, compound

HRID 505263Notes

Reaction equation

HRID 505263 reaction equation
[CH2:1]([NH:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:8][CH2:7]1)=O)[CH3:2].[BH4-].[Na+].C(O)(=O)C.N#N>C1COCC1>[CH2:1]([NH:3][CH2:4][C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:8][CH2:7]1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 947NitrogenHCID 4311764Sodium borohydrideHCID 178465145HCID 178465145, compound2×

Product 1

HCID 178464369HCID 178464369, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred suspension of methyl trans-4-[(ethylamino)carbonyl]cyclohexanecarboxylate (Intermediate 5, 430 mg, 2.01 mmol) and NaBH4 in THF (10 mL) was treated with acetic acid (1.6 mL) and heated at reflux for 16 h an atmosphere of N2. The reaction was cooled to room temperature, quenched with H2O (1 mL) and diluted with 1N NaOH (15 mL). The mixture was extracted with EtOAc (3×40 mL) and the combined extracts were washed with brine (40 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash silica gel chromatography (0-25% EtOAc/hexanes gradient) to afford methyl trans-4-[(ethylamino)methyl]cyclohexanecarboxylate as a clear oil. LCMS=200.2 (M+)+. 1H NMR (CDCl3, 500 MHz): δ 3.67 (s, 3H), 2.67-2.64 (q, J=7.1 Hz, 2H), 2.49-2.46 (m, 2H), 2.28-2.24 (m, 1H), 2.16-1.86 (m, 4H), 1.49-1.41 (m, 2H), 1.12 (t, J=5.5 Hz, 3H), 1.03 (m, 2H).

Workup

  1. temperatureheated
  2. customquenched with H2O (1 mL)
  3. additiondiluted with 1N NaOH (15 mL)
  4. extractionThe mixture was extracted with EtOAc (3×40 mL)
  5. washthe combined extracts were washed with brine (40 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash silica gel chromatography (0-25% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-e7eb3c41cc5a462d853990d59921cf22
Source dataset
uspto-grants-2010_08
Patent number
US07781426B2

Reaction notes

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