dimethyl (1R,2R)-cyclopropane-1,2-dicarboxylate

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

Procedure: Starting from dimethyl trans-1,2-cyclopropanedicarboxylate, trans-N-tert-butyloxycarbonyl-1,2-cyclopropanediamin hydrochloride may be prepared and purified analogously to cis-N-tert-butyloxycarbonyl-1,2-cyclopropanediamin hydrochloride (see 58.4). M.p: 200-202° C. may be prepared purified analogously to cis-N-tert-butyloxycarbonyl-1,2-cyclopropanediamin hydrochloride (see 58.4)

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

Procedure: Suspend trans-cyclopropane-1,2-dicarboxylic acid dimethylester (59.8 g, 0.378 mol) is suspended in 1.0N phosphate buffer (1.5 L, pH=7) add pig liver esterase (2.25 mL, 7500 units), and monitor NaOH consumption with a pH meter to control the reaction. After 3 h the consumption of 189 mL of 2N NaOH indicates the complete hydrolysis of the diester to the monomethylester. Acidified the clear solution by the addition of SN HCl to a pH=1. Separate the enzyme by addition of dichloromethane (500 mL) and diatomaceous earth (25 g). Stir for 5 min, and then filter the mixture. Saturate the filtrate with NaCl, and extract with ethyl acetate (5 times). Combine the extracts, dry (Na2SO4) and evaporate to obtain 50.8 g (93%) of solid, mp 46-47° C., m/z=45 (M+H)+ add pig liver esterase (2.25 mL, 7500 units) NaOH consumption with a pH meter the reaction After 3 h the consumption of 189 mL of 2N NaOH the complete hydrolysis of the diester to the monomethylester Separate the enzyme by addition of dichloromethane (500 mL) and diatomaceous earth (25 g) filter the mixture Saturate the filtrate with NaCl extract with ethyl acetate (5 times) Combine the extracts, dry (Na2SO4) evaporate

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

Procedure: Suspend trans-cyclopropane-1,2-dicarboxylic acid dimethylester (59.8 g, 0.378 mol) is suspended in 1.0N phosphate buffer (1.5 L, pH=7) add pig liver esterase (2.25 mL, 7500 units), and monitor NaOH consumption with a pH meter to control the reaction. After 3 h the consumption of 189 mL of 2N NaOH indicates the complete hydrolysis of the diester to the monomethylester. Acidified the clear solution by the addition of 5N HCl to a pH=1. Separate the enzyme by addition of dichloromethane (500 mL) and diatomaceous earth (25 g). Stir for 5 min, and then filter the mixture. Saturate the filtrate with NaCl, and extract with ethyl acetate (5 times). Combine the extracts, dry (Na2SO4) and evaporate to obtain 50.8 g (93%) of solid, mp 46–47° C., m/z=145 (M+H)+ add pig liver esterase (2.25 mL, 7500 units) NaOH consumption with a pH meter the reaction After 3 h the consumption of 189 mL of 2N NaOH the complete hydrolysis of the diester to the monomethylester Separate the enzyme by addition of dichloromethane (500 mL) and diatomaceous earth (25 g) filter the mixture Saturate the filtrate with NaCl extract with ethyl acetate (5 times) Combine the extracts, dry (Na2SO4) evaporate

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

Procedure: Suspend trans-cyclopropane-1,2-dicarboxylic acid dimethylester (59.8 g, 0.378 mol) is suspended in 1.0N phosphate buffer (1.5 L, pH=7) add pig liver esterase (2.25 mL, 7500 units), and monitor NaOH consumption with a pH meter to control the reaction. After 3 h the consumption of 189 mL of 2N NaOH indicates the complete hydrolysis of the diester to the monomethylester. Acidified the clear solution by the addition of 5N HCl to a pH=1. Separate the enzyme by addition of dichloromethane (500 mL) and diatomaceous earth (25 g). Stir for 5 min, and then filter the mixture. Saturate the filtrate with NaCl, and extract with ethyl acetate (5 times). Combine the extracts, dry (Na2SO4) and evaporate to obtain 50.8 g (93%) of solid, mp 46–47° C., m/z=145 (M+H)+ add pig liver esterase (2.25 mL, 7500 units) NaOH consumption with a pH meter the reaction After 3 h the consumption of 189 mL of 2N NaOH the complete hydrolysis of the diester to the monomethylester Separate the enzyme by addition of dichloromethane (500 mL) and diatomaceous earth (25 g) filter the mixture Saturate the filtrate with NaCl extract with ethyl acetate (5 times) Combine the extracts, dry (Na2SO4) evaporate

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

Procedure: Starting from dimethyl trans-1,2-cyclopropanedicarboxylate, trans-N-tert-butyloxycarbonyl-1,2-cyclopropanediamin hydrochloride may be prepared and purified analogously to cis-N-tert-butyloxycarbonyl-1,2-cyclopropanediamin hydrochloride (see 58.4). M.p: 200-202° C. may be prepared purified analogously to cis-N-tert-butyloxycarbonyl-1,2-cyclopropanediamin hydrochloride (see 58.4)

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

Procedure: Suspend trans-cyclopropane-1,2-dicarboxylic acid dimethylester (59.8 g, 0.378 mol) is suspended in 1.0N phosphate buffer (1.5 L, pH=7) add pig liver esterase (2.25 mL, 7500 units), and monitor NaOH consumption with a pH meter to control the reaction. After 3 h the consumption of 189 mL of 2N NaOH indicates the complete hydrolysis of the diester to the monomethylester. Acidified the clear solution by the addition of 5N HCl to a pH=1. Separate the enzyme by addition of dichloromethane (500 mL) and diatomaceous earth (25 g). Stir for 5 min, and then filter the mixture. Saturate the filtrate with NaCl, and extract with ethyl acetate (5 times). Combine the extracts, dry (Na2SO4) and evaporate to obtain 50.8 g (93%) of solid, mp 46-47° C., m/z=145 (M+H)+ add pig liver esterase (2.25 mL, 7500 units) NaOH consumption with a pH meter the reaction After 3 h the consumption of 189 mL of 2N NaOH the complete hydrolysis of the diester to the monomethylester Separate the enzyme by addition of dichloromethane (500 mL) and diatomaceous earth (25 g) filter the mixture Saturate the filtrate with NaCl extract with ethyl acetate (5 times) Combine the extracts, dry (Na2SO4) evaporate

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

Procedure: Suspend trans-cyclopropane-1,2-dicarboxylic acid dimethylester (59.8 g, 0.378 mol) is suspended in 1.0N phosphate buffer (1.5 L, pH=7) add pig liver esterase (2.25 mL, 7500 units), and monitor NaOH consumption with a pH meter to control the reaction. After 3 h the consumption of 189 mL of 2N NaOH indicates the complete hydrolysis of the diester to the monomethylester. Acidified the clear solution by the addition of 5N HCl to a pH=1. Separate the enzyme by addition of dichloromethane (500 mL) and diatomaceous earth (25 g). Stir for 5 min, and then filter the mixture. Saturate the filtrate with NaCl, and extract with ethyl acetate (5 times). Combine the extracts, dry (Na2SO4) and evaporate to obtain 50.8 g (93%) of solid, mp 46-47° C., m/z=145 (M+H)+ add pig liver esterase (2.25 mL, 7500 units) NaOH consumption with a pH meter the reaction After 3 h the consumption of 189 mL of 2N NaOH the complete hydrolysis of the diester to the monomethylester Separate the enzyme by addition of dichloromethane (500 mL) and diatomaceous earth (25 g) filter the mixture Saturate the filtrate with NaCl extract with ethyl acetate (5 times) Combine the extracts, dry (Na2SO4) evaporate

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

Procedure: Suspend trans-cyclopropane-1,2-dicarboxylic acid dimethylester (59.8 g, 0.378 mol) is suspended in 1.0N phosphate buffer (1.5 L, pH=7) add pig liver esterase (2.25 mL, 7500 units), and monitor NaOH consumption with a pH meter to control the reaction. After 3 h the consumption of 189 mL of 2N NaOH indicates the complete hydrolysis of the diester to the monomethylester. Acidified the clear solution by the addition of SN HCl to a pH=1. Separate the enzyme by addition of dichloromethane (500 mL) and diatomaceous earth (25 g). Stir for 5 min, and then filter the mixture. Saturate the filtrate with NaCl, and extract with ethyl acetate (5 times). Combine the extracts, dry (Na2SO4) and evaporate to obtain 50.8 g (93%) of solid, mp 46-47° C., m/z=45 (M+H)+ add pig liver esterase (2.25 mL, 7500 units) NaOH consumption with a pH meter the reaction After 3 h the consumption of 189 mL of 2N NaOH the complete hydrolysis of the diester to the monomethylester Separate the enzyme by addition of dichloromethane (500 mL) and diatomaceous earth (25 g) filter the mixture Saturate the filtrate with NaCl extract with ethyl acetate (5 times) Combine the extracts, dry (Na2SO4) evaporate

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

Procedure: Suspend trans-cyclopropane-1,2-dicarboxylic acid dimethylester (59.8 g, 0.378 mol) is suspended in 1.0N phosphate buffer (1.5 L, pH=7) add pig liver esterase (2.25 mL, 7500 units), and monitor NaOH consumption with a pH meter to control the reaction. After 3 h the consumption of 189 mL of 2N NaOH indicates the complete hydrolysis of the diester to the monomethylester. Acidified the clear solution by the addition of 5N HCl to a pH=1. Separate the enzyme by addition of dichloromethane (500 mL) and diatomaceous earth (25 g). Stir for 5 min, and then filter the mixture. Saturate the filtrate with NaCl, and extract with ethyl acetate (5 times). Combine the extracts, dry (Na2SO4) and evaporate to obtain 50.8 g (93%) of solid, mp 46–47° C., m/z=145 (M+H)+ add pig liver esterase (2.25 mL, 7500 units) NaOH consumption with a pH meter the reaction After 3 h the consumption of 189 mL of 2N NaOH the complete hydrolysis of the diester to the monomethylester Separate the enzyme by addition of dichloromethane (500 mL) and diatomaceous earth (25 g) filter the mixture Saturate the filtrate with NaCl extract with ethyl acetate (5 times) Combine the extracts, dry (Na2SO4) evaporate

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

Procedure: Starting from dimethyl trans-1,2-cyclopropanedicarboxylate, trans-N-tert-butyloxycarbonyl-1,2-cyclopropanediamin hydrochloride may be prepared and purified analogously to cis-N-tert-butyloxycarbonyl-1,2-cyclopropanediamin hydrochloride (see 58.4). M.p: 200-202° C. may be prepared purified analogously to cis-N-tert-butyloxycarbonyl-1,2-cyclopropanediamin hydrochloride (see 58.4)