3-amino-1-phenylpropan-1-ol

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: reacting said α-(2-aminoethyl)benzenemethanol with a chloroformate or dicarbonate to form an N-(3-hydroxy-3-phenylpropyl)urethane;

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

Procedure: reacting said α-(2-aminoethyl)benzenemethanol with a chloroformate or dicarbonate to form an N-(3-hydroxy-3-phenylpropyl)urethane;

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-phenyl-3-hydroxypropylmethanesulfonate (1.71 g, Gao, et al., J. Org. Chem., 1988, 53, 4081), tetrahydrofuran (10 mL) and 28% ammonium hydroxide (30 mL) was heated in a bomb at 65° C. for 16 hours. After cooling, the volatiles were eliminated to leave the aqueous solution which was extracted with ether. The aqueous layer was concentrated under reduced pressure, azeotroped twice with anhydrous acetonitrile and dried under vacuum to give 3-amino-1-phenyl-1-propanol (1.04 g) as a white solid: mp 92-94° C., Rf=0.1 (silica, methanol/ethyl acetate 1/1). After cooling to leave the aqueous solution which was extracted with ether The aqueous layer was concentrated under reduced pressure azeotroped twice with anhydrous acetonitrile dried under vacuum

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

Procedure: reacting said α-(2-aminoethyl)benzenemethanol with a chloroformate or dicarbonate to form an N-(3-hydroxy-3-phenylpropyl)urethane;

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

Procedure: reacting said α-(2-aminoethyl)benzenemethanol with a chloroformate or dicarbonate to form an N-(3-hydroxy-3-phenylpropyl)urethane;

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 compounds of formula (I) may be prepared by condensing an acetophenone of general formula (II): ##STR3## (in which R1 and R2 are as defined above) in a Mannich reaction with formaldehyde and a primary or secondary amine, reducing the amino-ketone thus formed to a 3-amino-1-phenyl-propan-1-ol, and subsequently dehydrating this 3-amino-1-phenyl-propan-1-ol. The compound so produced is of general formula (I) in which A is CH=CH; subsequently, if desired, this compound may be hydrogenated to produce a compound of formula (I) in which A is CH2CH2.

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

Procedure: The compounds of formula (I) may be prepared by condensing an acetophenone of general formula (II): ##STR3## (in which R1 and R2 are as defined above) in a Mannich reaction with formaldehyde and a primary or secondary amine, reducing the amino-ketone thus formed to a 3-amino-1-phenyl-propan-1-ol, and subsequently dehydrating this 3-amino-1-phenyl-propan-1-ol. The compound so produced is of general formula (I) in which A is CH=CH; subsequently, if desired, this compound may be hydrogenated to produce a compound of formula (I) in which A is CH2CH2.