Ethyl Acetate → HCID 178459251, compound

HRID 1483823Notes

Reaction equation

HRID 1483823 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6](C(OC)=O)[CH2:5][CH2:4]1.[CH3:13][Mg]Br.CC(=O)[O:18][CH2:19][CH3:20]>C1COCC1>[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:19]([OH:18])([CH3:20])[CH3:13])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 178418573HCID 178418573, compoundHCID 178501118HCID 178501118, compound

Product 1

HCID 178459251HCID 178459251, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-methyl 4-(aminomethyl)cyclohexanecarboxylate (1 g, 5.8 mmol) in THF (50 mL) was added dropwise methylmagnesium bromide (7.7 mL, 23.2 mmol) at −78° C. The mixture was stirred at room temperature for 2 h. TLC (PE:EA=5:1) showed the reaction was complete. The mixture was quenched by the addition of NH4Cl (100 mL) and extracted with EtOAc (100 mL×3). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo to give 2-(trans-4-(aminomethyl)cyclohexyl)propan-2-ol (0.42 g, 39.2%) as a yellow solid.

Workup

  1. customThe mixture was quenched by the addition of NH4Cl (100 mL)
  2. extractionextracted with EtOAc (100 mL×3)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f63658df14b44c2da1a8e4a8841c34f9
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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