1-ethenylcyclopentan-1-ol

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

Procedure: Obtained by a procedure similar to that described in Example 1, from 3-(N-benzyloxycarbonyl-2(R)-pyrrolidinylmethyl)-5-bromo-1H-indole (Preparation 1) and 1-vinylcyclopentanol (Example 5(a)), as a foam. Rf 0.40 (SS 10). [α]D25 -31° (c=0.1, CH3OH). Found: C,75.58; H,7.24; N,6.22. C28H32N2O3 requires C,75.64; H,7.26; N,6.30%. Obtained by a procedure similar to

Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 600 ml autoclave containing a mixture of 1-ethenyl-cyclopentanol (172.0 g; 1.54 mol), isopropenyl methyl ether (218.8 g; 3.04 mol), triethylamine (1.65 ml) and 85% H3PO4 (0.72 ml) was pressurized with N2 at 2 bar and heated up to 125° C. An increase of the pressure to 7 bar was observed. After 14 hours stirring, the autoclave was cooled down to room temperature and depressurized. MTBE (1.5 l) was added to the mixture, washed with H2O (4×25 ml) until neutral pH, dried (MgSO4) and concentrated. Distillation (61° C./0.1 torr) yielded 161.3 g (69% yield) of 5-cyclopentylidenepentan-2-one. A 600 ml autoclave containing An increase of the pressure to 7 bar the autoclave was cooled down to room temperature washed with H2O (4×25 ml) until neutral pH dried (MgSO4) concentrated Distillation (61° C./0.1 torr)

Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 600 ml autoclave containing a mixture of 1-ethenyl-cyclopentanol (172.0 g; 1.54 mol), isopropenyl methyl ether (218.8 g; 3.04 mol), triethylamine (1.65 ml) and 85% H3PO4 (0.72 ml) was pressurized with N2 at 2 bar and heated up to 125° C. An increase of the pressure to 7 bar was observed. After 14 hours stirring, the autoclave was cooled down to room temperature and depressurized. MTBE (1.5 l) was added to the mixture, washed with H2O (4×25 ml) until neutral pH, dried (MgSO4) and concentrated. Distillation (61° C./0.1 torr) yielded 161.3 g (69% yield) of 5-cyclopentylidenepentan-2-one. A 600 ml autoclave containing An increase of the pressure to 7 bar the autoclave was cooled down to room temperature washed with H2O (4×25 ml) until neutral pH dried (MgSO4) concentrated Distillation (61° C./0.1 torr)

Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 600 ml autoclave containing a mixture of 1-ethenyl-cyclopentanol (172.0 g; 1.54 mol), isopropenyl methyl ether (218.8 g; 3.04 mol), triethylamine (1.65 ml) and 85% H3PO4 (0.72 ml) was pressurized with N2 at 2 bar and heated up to 125° C. An increase of the pressure to 7 bar was observed. After 14 hours stirring, the autoclave was cooled down to room temperature and depressurized. MTBE (1.5 l) was added to the mixture, washed with H2O (4×25 ml) until neutral pH, dried (MgSO4) and concentrated. Distillation (61° C./0.1 torr) yielded 161.3 g (69% yield) of 5-cyclopentylidenepentan-2-one. A 600 ml autoclave containing An increase of the pressure to 7 bar the autoclave was cooled down to room temperature washed with H2O (4×25 ml) until neutral pH dried (MgSO4) concentrated Distillation (61° C./0.1 torr)

Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 600 ml autoclave containing a mixture of 1-ethenyl-cyclopentanol (172.0 g; 1.54 mol), isopropenyl methyl ether (218.8 g; 3.04 mol), triethylamine (1.65 ml) and 85% H3PO4 (0.72 ml) was pressurized with N2 at 2 bar and heated up to 125° C. An increase of the pressure to 7 bar was observed. After 14 hours stirring, the autoclave was cooled down to room temperature and depressurized. MTBE (1.5 1) was added to the mixture, washed with H2O (4×25 ml) until neutral pH, dried (MgSO4) and concentrated. Distillation (61° C./0.1 torr) yielded 161.3 g (69% yield) of 5-cyclopentylidenepentan-2-one. A 600 ml autoclave containing An increase of the pressure to 7 bar the autoclave was cooled down to room temperature washed with H2O (4×25 ml) until neutral pH dried (MgSO4) concentrated Distillation (61° C./0.1 torr)

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In an autoclave under N2, a mixture of 1-vinylcyclopentanol (65 g, 0.58 mol), 2-methoxypropene (108 ml, 1.15 mol), 85% phosphoric acid (0.29 ml), triethylamine (0.63 ml) was heated at 130° C. for 15 h. The reaction mixture was cooled to 20° C., diluted with MTBE (500 ml), washed three times with water (25 ml), once with a saturated aqueous solution of NaCl (25 ml), dried (MgSO4) and concentrated. Widmer-Distillation (0.13 mbar, head temp. 58° C.) of the crude product gave 5-cyclopentylidenepentan-2-one (63.67 g, 72%). The reaction mixture was cooled to 20° C. washed three times with water (25 ml) once with a saturated aqueous solution of NaCl (25 ml), dried (MgSO4) concentrated Widmer-Distillation (0.13 mbar, head temp. 58° C.) of the crude product

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

Procedure: Obtained by a procedure similar to that described in Example 1, from 3-(N-benzyloxycarbonyl-2(R)-pyrrolidinylmethyl)-5-bromo-1H-indole (Preparation 1) and 1-vinylcyclopentanol (Example 5(a)), as a foam. Rf 0.40 (SS 10). [α]D25 -31° (c=0.1, CH3OH). Found: C,75.58; H,7.24; N,6.22. C28H32N2O3 requires C,75.64; H,7.26; N,6.30%. Obtained by a procedure similar to