Sodium Hydroxide → HCID 178453942, compound

HRID 1984936Notes

Reaction equation

HRID 1984936 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([C:14](=O)[NH2:15])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:9][CH2:10][C@@H:11]([CH2:14][NH2:15])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178453949HCID 178453949, compound

Product 1

HCID 178453942HCID 178453942, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of cis-(4-carbamoyl-cyclohexyl)-carbamic acid tert-butyl ester obtained in step B of example 2332 (9.68 g, 40 mmol) in THF (100 mL) was added a solution of 1 M BH3 in THF (80 mL, 80 mmol) over 30 min. The mixture was stirred at reflux for 2 hr. After cooling the reaction mixture to ambient temperature, 1 M aqueous sodium hydroxide was carefully added. The solvents were removed under reduced pressure and the aqueous layer was extracted with CH2Cl2 (twice). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give cis-(4-aminomethyl-cyclohexyl)-carbamic acid tert-butyl ester as colorless oil (5.16 g, 57%).

Workup

  1. temperatureat reflux for 2 hr
  2. customThe solvents were removed under reduced pressure
  3. extractionthe aqueous layer was extracted with CH2Cl2 (twice)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-74d15e7f7c394317966b966fdd9a0a33
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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