Hydrochloric Acid → (1S,2R)-Methyl 2-aminocyclohexanecarboxylate
Reaction equation
Cl.[CH3:2][O:3][C:4]([C@H:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]1[NH:12]C(OC(C)(C)C)=O)=[O:5].C1(C)C=CC=CC=1>O1CCOCC1>[CH3:2][O:3][C:4]([C@H:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]1[NH2:12])=[O:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A 4.0 M solution of hydrochloric acid in 1,4-dioxane (20 mL) was added to a solution of (1S,2R)-2-tert-butoxycarbonylamino-1-cyclohexanecarboxylic acid methyl ester (1.28 g, 4.97 mmol) in 1,4-dioxane (15 mL) at 25° C. The reaction mixture was stirred at 25° C. for 2 h, then toluene (40 mL) was added and the volatiles were removed in vacuo. The residue was partitioned between saturated sodium bicarbonate solution (150 mL) and ethyl acetate (2×150 mL). The combined organic layers were dried over sodium sulfate, decanted, and were concentrated in vacuo to afford the crude product, (1S,2R)-2-amino-cyclohexanecarboxylic acid methyl ester as a yellow oil, which was used directly in the next step without further purification.
Workup
- customthe volatiles were removed in vacuo
- customThe residue was partitioned between saturated sodium bicarbonate solution (150 mL) and ethyl acetate (2×150 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- customdecanted
- concentrationwere concentrated in vacuo
Sources & evidence
- ORD record
- ord-1de79ac0fc3241ac8f17cf7535f0dbd8
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582626B2
Reaction notes
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