4-[(dimethylamino)methyl]phenol

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

Procedure: The title compound was prepared by substituting 4-hydroxybenzaldehyde for 4′-chlorobiphenyl-2-carboxaldehyde and dimethylamine for tert-butyl piperazine-1-carboxylate in EXAMPLE 1A.

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

Procedure: Using a similar protocol as described in Example 29C employing 4-((dimethylamino)methyl)phenol (8.4 g, 55.5 mmol) and tert-butyl 3-(methylsulfonyloxy)azetidine-1-carboxylate (16.8 g, 66.7 mmol) as starting materials afforded 14.8 g (75%) of 33A as an oil. 1H NMR (500 MHz, CDCl3): δ 1.40 (s, 9H), 2.55 (s, 6H), 3.90 (s, 2H), 4.00 (m, 2H), 4.30 (m, 2H), 4.85 (m, 1H), 6.75 (d, 2H), 7.35 (d, 2H), MS (APCI+) m/z 307 [M+H]+.

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

Procedure: The title compound was prepared by substituting 4-hydroxybenzaldehyde for 4′-chlorobiphenyl-2-carboxaldehyde and dimethylamine for tert-butyl piperazine-1-carboxylate in EXAMPLE 1A.

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

Procedure: The title compound was prepared by substituting 4-hydroxybenzaldehyde for 4′-chlorobiphenyl-2-carboxaldehyde and dimethylamine for tert-butyl piperazine-1-carboxylate in EXAMPLE 1A.

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

Procedure: The title compound was prepared by substituting 4-hydroxybenzaldehyde for 4′-chlorobiphenyl-2-carboxaldehyde and dimethylamine for tert-butyl piperazine-1-carboxylate in EXAMPLE 1A.

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

Procedure: The title compound was prepared by substituting 4-hydroxybenzaldehyde for 4′-chlorobiphenyl-2-carboxaldehyde and dimethylamine for tert-butyl piperazine-1-carboxylate in EXAMPLE 1A.

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

Procedure: Using a similar protocol as described in Example 29C employing 4-((dimethylamino)methyl)phenol (8.4 g, 55.5 mmol) and tert-butyl 3-(methylsulfonyloxy)azetidine-1-carboxylate (16.8 g, 66.7 mmol) as starting materials afforded 14.8 g (75%) of 33A as an oil. 1H NMR (500 MHz, CDCl3): δ 1.40 (s, 9H), 2.55 (s, 6H), 3.90 (s, 2H), 4.00 (m, 2H), 4.30 (m, 2H), 4.85 (m, 1H), 6.75 (d, 2H), 7.35 (d, 2H), MS (APCI+) m/z 307 [M+H]+.

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

Procedure: The title compound was prepared by substituting 4-hydroxybenzaldehyde for 4′-chlorobiphenyl-2-carboxaldehyde and dimethylamine for tert-butyl piperazine-1-carboxylate in EXAMPLE 1A.

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

Procedure: The title compound was prepared by substituting 4-hydroxybenzaldehyde for 4′-chlorobiphenyl-2-carboxaldehyde and dimethylamine for tert-butyl piperazine-1-carboxylate in EXAMPLE 1A.