Sodium Hydroxide → HCID 66764746, compound

HRID 2363898Notes

Reaction equation

HRID 2363898 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[O:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1.[OH-].[Na+]>ClCCl>[NH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[O:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68603153HCID 68603153, compound

Product 1

HCID 66764746HCID 66764746, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1R,2R)-2-amino-1-(3,4-dimethoxyphenethoxy)cyclohexane hydrochloride (32) (474 mg, 1.50 mmol, 99.4% ee) was partitioned between 6M aq NaOH (1 mL) and dichloromethane (4 mL). The aqueous layer was collected and extracted once more with dichloromethane (4 mL). The combined organic extracts were dried over anhydrous MgSO4 and concentrated in vacuo to give (1R,2R)-2-amino-1-(3,4-dimethoxyphenethoxy)cyclohexane as an orange oil (370 mg, 88% yield).

Workup

  1. customThe aqueous layer was collected
  2. extractionextracted once more with dichloromethane (4 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-982d75b785e14c7b9d78c100814c6757
Source dataset
uspto-grants-2014_04
Patent number
US08692002B2

Reaction notes

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