Hydrochloric Acid → Benzyl 3-(2-aminocyclohexyl)-3-hydroxyazetidine-1-carboxylate

HRID 1808996Notes

Reaction equation

HRID 1808996 reaction equation
[OH:1][C:2]1([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]2=O)[CH2:5][N:4]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:3]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:29].[Na+].Cl>CO>[CH2:9]([O:8][C:6]([N:4]1[CH2:5][C:2]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[NH2:29])([OH:1])[CH2:3]1)=[O:7])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 67051703Benzyl 3-hydroxy-3-(2-oxocyclohexyl)azetidine-1-carboxylate

Product 1

HCID 67051790Benzyl 3-(2-aminocyclohexyl)-3-hydroxyazetidine-1-carboxylateYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of benzyl 3-hydroxy-3-(2-oxocyclohexyl)azetidine-1-carboxylate (100 mg, 330 mmol) in methanol (1.60 mL) in the presence of ammonium acetate (191 mg, 2.48 mmol was cooled to 0° C. for 1 hour. Sodium cyanoborohydride (81.5 mg, 1.30 mmol) was added and the mixture was stirred at room temperature for 16 hours. To the reaction mixture was added 6 N hydrogen chloride (800 μL) and extracted with ethyl acetate. The aqueous layer was basified with aqueous sodium bicarbonate (pH 9) and extracted with dichloromethane. The combined organic portion was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford benzyl-3-(2-aminocyclohexyl)-3-hydroxyazetidine-1-carboxylate (73.7 mg, 73%). MS (EI) for C17H24N2O3: 305 (MH+).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic portion was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-031ad104c3fa454a9db9b9ab782b5c62
Source dataset
uspto-grants-2013_01
Patent number
US08362002B2

Reaction notes

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