2-amino-1-(3-fluorophenyl)ethanol

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:

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

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

Procedure: The title compound was prepared in the manner described in Example 3 replacing 2-(3-chlorophenyl)-2-hydroxyethanamine with 2-(3-fluorophenyl)-2-hydroxyethanamine. The chromatographed material was treated with methanolic fumaric acid and the derived salt recrystallised from ethyl acetate to give the title compound (fumarate), mp 58-83, as a 52-48 mixture of diastereoisomers. The title compound was prepared in the manner the derived salt recrystallised from ethyl acetate

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

Procedure: The title compound was prepared in the manner described in Example 3 replacing 2-(3-chlorophenyl)-2-hydroxyethanamine with 2-(3-fluorophenyl)-2-hydroxyethanamine. The chromatographed material was treated with methanolic fumaric acid and the derived salt recrystallised from ethyl acetate to give the title compound (fumarate), mp 58-83, as a 52-48 mixture of diastereoisomers. The title compound was prepared in the manner the derived salt recrystallised from ethyl acetate

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

Procedure: This was prepared in an identical manner to the compound described in Example 1 using 2-hydroxy-2-(3-fluorophenyl) ethanamine (1.55 g) and 4{(E)-2-carbomethoxyethenyl}phenylpropan-2-one (2.18 g). Elution with 1% methanolchloroform on Kieselgel 60 gave the title compound (1.4 g) m.p. 75°-110° C. (benzene-heptane) as an ~45:55 mixture of diastereoisomers. τ(CDCl3) 8.9 (3H, d, J=6 Hz), 6.9-7.8 (7H, m, 2H disappears with D2O), 6.25 (3H, s), 5.45 (1H, m), 3.6 (1H, d, J=16 Hz), 2.55-3.2 (8H, m), 2.35 (1H, d, J=16 Hz). This was prepared in an identical manner to the compound Elution with 1% methanolchloroform on Kieselgel 60

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

Procedure: The title compound was prepared in the manner described in Example 3 replacing 2-(3-chlorophenyl)-2-hydroxyethanamine with 2-(3-fluorophenyl)-2-hydroxyethanamine. The chromatographed material was treated with methanolic fumaric acid and the derived salt recrystallised from ethyl acetate to give the title compound (fumarate), mp 58-83, as a 52-48 mixture of diastereoisomers. The title compound was prepared in the manner the derived salt recrystallised from ethyl acetate

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: Following a procedure similar to that described in Example 6, but using 2 g of 2-amino-1-(3-fluorophenyl)ethanol (prepared as described in Preparation 13), 3.44 g of methyl 4-(2-oxopropoxy)phenylacetate (prepared as described in Preparation 3), 60 ml of benzene, 60 ml of absolute methanol and 3.6 g of sodium cyanoborohydride, 1.18 g of the title compound were obtained as crystals, melting at 52° C.