ethyl 2-hydroxycyclohexane-1-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.2 g of borane/tert-butylamine complex was added to 200 ml of diethyl ether solution containing 17.0 g (0.10 mol) of ethyl cyclohexanone-2-carboxylate and stirred overnight at room temperature. An aqueous diluted hydrochloric acid was added thereto to make it weakly acidic, which was then subjected to liquid-liquid separation. The organic layer thus separated was dried, concentrated and then distilled under reduced pressure to obtain 13.5 g of ethyl 2-hydroxycyclohexanecarboxylate. Yield: 78.5%. b.p. 68° to 71° C. (0.2 mmHg). which was then subjected to liquid-liquid separation The organic layer thus separated was dried concentrated distilled under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.2 g of borane/tert-butylamine complex was added to 200 ml of diethyl ether solution containing 17.0 g (0.10 mol) of ethyl cyclohexanone-2-carboxylate and stirred overnight at room temperature. An aqueous diluted hydrochloric acid was added thereto to make it weakly acidic, which was then subjected to liquid-liquid separation. The organic layer thus separated was dried, concentrated and then distilled under reduced pressure to obtain 13.5 g of ethyl 2-hydroxycyclohexanecarboxylate. Yield: 78.5%. b.p. 68° to 71° C. (0.2 mmHg). which was then subjected to liquid-liquid separation The organic layer thus separated was dried concentrated distilled under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.2 g of borane/tert-butylamine complex was added to 200 ml of diethyl ether solution containing 15.6 g (0.10 mol) of methyl cyclohexanone-2-carboxylate and stirred overnight at room temperature. An aqueous diluted hydrochloric acid was added thereto to make it weakly acidic, which was then subjected to liquid-liquid separation. The organic layer separated was dried, concentrated and then distilled under reduced pressure to obtain 13.4 g of ethyl 2-hydroxycyclohexanecarboxylate. Yield: 84.8%. b.p. 60° to 62° C. (0.3 mmHg). which was then subjected to liquid-liquid separation The organic layer separated was dried concentrated distilled under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The asymmetric reduction of ethyl 2-oxocyclohexanecarboxylate was carried out by using this reductase (2). Namely, 4 ml of the reaction mixture containing the reductase (2) (2U), NADPH (0.8 μmol), ethyl 2-oxocyclohexanecarboxylate (100 μmol, 17 mg), phosphate buffer solution (pH 7.0, 400 μmol), glucose dehydrogenase (the same enzyme as that used in Example 4; 2U) and glucose (100,μmol) was incubated at 30° C. with gentle shaking to promote the reaction. After 4 hour-incubation, the reaction mixture was extracted according to the same manner as in Example 3. The extract was analyzed by gas chromatography described in Example 1. As a result, the yield of the cis isomer was 17.0 mg (reduction yield >99%), and neither the remaining substrate nor the trans isomer was detected. On the other hand, the extract above was distilled off according to the the same manner as in Example 3 to obtain the reduction product, ethyl 2-hydroxycyclohexanecarboxylate. The resulting reduction product was analyzed by high performance liquid chromatography described in Example 1. As a result, only the cis 2 isomer was detected and no other isomers were detected. was incubated at 30° C. the reaction the reaction mixture was extracted On the other hand, the extract above was distilled off

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.2 g of borane/tert-butylamine complex was added to 200 ml of diethyl ether solution containing 17.0 g (0.10 mol) of ethyl cyclohexanone-2-carboxylate and stirred overnight at room temperature. An aqueous diluted hydrochloric acid was added thereto to make it weakly acidic, which was then subjected to liquid-liquid separation. The organic layer thus separated was dried, concentrated and then distilled under reduced pressure to obtain 13.5 g of ethyl 2-hydroxycyclohexanecarboxylate. Yield: 78.5%. b.p. 68° to 71° C. (0.2 mmHg). which was then subjected to liquid-liquid separation The organic layer thus separated was dried concentrated distilled under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.2 g of borane/tert-butylamine complex was added to 200 ml of diethyl ether solution containing 15.6 g (0.10 mol) of methyl cyclohexanone-2-carboxylate and stirred overnight at room temperature. An aqueous diluted hydrochloric acid was added thereto to make it weakly acidic, which was then subjected to liquid-liquid separation. The organic layer separated was dried, concentrated and then distilled under reduced pressure to obtain 13.4 g of ethyl 2-hydroxycyclohexanecarboxylate. Yield: 84.8%. b.p. 60° to 62° C. (0.3 mmHg). which was then subjected to liquid-liquid separation The organic layer separated was dried concentrated distilled under reduced pressure