Hydrochloric Acid → HCID 178461366, compound

HRID 2111694Notes

Reaction equation

HRID 2111694 reaction equation
C[C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]([C@@H:11]1[CH2:13][C@H:12]1[C:14]([OH:16])=O)=[O:10].B(OC)(OC)O[CH3:19].C1COCC1.Cl>>[CH3:19][C@H:6]1[CH2:7][CH2:2][C@H:3]([NH:8][C:9]([C@@H:11]2[CH2:13][C@H:12]2[CH2:14][OH:16])=[O:10])[CH2:4][CH2:5]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8470Trimethyl borateHCID 68455212trans-2-(trans-2-Methylcyclohexylcarbamoyl)-cyclopropanecarboxylic acid

Product 1

HCID 178461366HCID 178461366, compoundYield 83%

Procedure

Stir a solution, under argon, at 0° C., of trans-2-(trans-2-methylcyclohexylcarbamoyl)-cyclopropanecarboxylic acid (Example 11b) (3.69 g, 16.4 mmol), trimethyl borate (5.6 mL, 50 mmol), and add slowly 2N borane dimethylsulfide complex in THF (16.4 mL, 32.8 mmol). Continue to stir the reaction at 0° C. for 1 h, and then at ambient temperature for 2 h. Carefully pour the reaction mixture into ice-H2O and acidify with 2N HCl. Extract the mixture with EtOAc (3 times), wash with brine, dry over MgSO4 and concentrate to obtain 2.85 g (83%) of product as a solid.

Workup

  1. stirringContinue to stir
  2. customthe reaction at 0° C. for 1 h
  3. extractionExtract the mixture with EtOAc (3 times)
  4. washwash with brine
  5. dry with materialdry over MgSO4
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-a28b07d6bc4b4845989778763729fb99
Source dataset
uspto-grants-2009_04
Patent number
US07521445B2

Reaction notes

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