(2S)-2-(dibenzylamino)propanal

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

Procedure: Dry DMSO (0.53 ml, 7.43 mmol) was added to a stirred solution of oxalyl chloride (0.31 ml, 3.6 mmol) in CH2Cl2 (7.5 ml) at −78° C. The solution was allowed to stir 15 minutes followed by the addition of 40 (740 mg, 2.90 mmol) in CH2Cl2 (7.5 ml). After 30 minutes, Et3N (1.0 ml, 7.2 mmol) was added and allowed to warm to room temperature. The solution was extracted with saturated. NaHCO3 (20 ml) and the aqueous layer was extracted with CH2Cl2 (2×15 ml). The organic layer was washed with saturated NaCl solution, dried with MgSO4 an concentrated in vacuo at room temperature to give 720 mg (98% yield) of a yellow oil which became a solid when cooled to −20° C. The aldehyde was used without further purification. mp 52-54° C., Literature mp 55.5° C. See, Dix et al., Arch Pharm (Weinheim) 1995, 328, 203-205.; [α]26D=−36.0 (c 1, CHCl3 Literature [α]20D=−35.1 (c 1, EtOAc); 1H NMR (400 MHz, CDCl3) δ1.19 (d, 2H, J=7.0 Hz), 3.34 (q, 1H, J=7.0 Hz), 3.58 (d, 2H, J=13.7 Hz), 3.74 (d, 2H, J=13.7 Hz), 7.26 (m, 2H), 7.33 (m, H), 7.42 (m, 4H), 9.74 (s, 1H); 13C NMR (100 MHz) δ6.7, 54.9, 62.8, 3.3, 4.4, 4.8, 139.1, 204.6; FABMS m/z 408.2 (M+MB), 254.2 (M+H), 22.2 (M-CHO); HRFABMS Calcd. for C17H20NO Mr 254.1545 (M+H). Found Mr 254.1545. After 30 minutes The solution was extracted with saturated NaHCO3 (20 ml) and the aqueous layer was extracted with CH2Cl2 (2×15 ml) The organic layer was washed with saturated NaCl solution dried with MgSO4 an concentrated in vacuo at room temperature

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 3.0 M diethyl ether solution of ethylmagnesium bromide (7.3 ml, 21.8 mmol) is added under N2 at 0° C. to a 95 ml tetrahydrofuran solution of N-benzenesulfonyl-3-iodo-5,7-difluoro-indole (8.4 g, 20 mmol). The resulting mixture is stirred for 20 minutes at 0° C., allowed to warm to room temperature over 20 minutes, then recooled to 0° C. A 20 ml tetrahydrofuran solution of (S)N,N dibenzyl-2-aminopropanal (Syn. Lett., 1997,2, 223-224, 5.1 g, 22 mmol) is added to the reaction mixture and the resulting mixture is stirred 1 hour as it warmed to room temp. The reaction is quenched with aqueous NH4Cl, extracted with ethyl acetate, washed with brine, dried (Na2SO4), filtered, concentrated, and the residue is purified by flash chromatography (SiO2, ethyl acetate/hexane gradient) to yield 8.4 g of 2-(N,N-dibenzylamino)-1-(1-benzenesulfonyl-5,7-difluoro-1H-indol-3-yl)-propan-1-ol. (77%) to warm to room temperature over 20 minutes recooled to 0° C the resulting mixture is stirred 1 hour as it warmed to room temp The reaction is quenched with aqueous NH4Cl extracted with ethyl acetate washed with brine dried (Na2SO4) filtered concentrated the residue is purified by flash chromatography (SiO2, ethyl acetate/hexane gradient)

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

Procedure: According to the method of Example 26, from aldehyde 4 (380 mg, 1.50 mmol) and 1-bromononadecane (1.30 g, 3.75 mmol), alcohol 49 was obtained as a colorless oil (349 mg, 45% yield).

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

Procedure: According to the method of Example 26, from aldehyde 4 (380 mg, 1.50 mmol) and 1-bromononadecane (1.30 g, 3.75 mmol), alcohol 49 was obtained as a colorless oil (349 mg, 45% yield).

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

Procedure: According to the method of Example 26, from aldehyde 4 (350 mg, 1.38 mmol) and 1-bromooctadecane (1.15 g, 3.45 mmol), alcohol 46 was obtained as a colorless oil (395 mg, 56% yield).

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

Procedure: According to the method of Example 26, from aldehyde 4 (410 mg, 1.62 mmol) and 1-bromoheptadecane (2.07 g, 6.47 mmol), alcohol 44 was obtained as a colorless oil (427 mg, 53% yield).

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

Procedure: According to the method of Example 26, from aldehyde 4 (410 mg, 1.62 mmol) and 1-bromoheptadecane (2.07 g, 6.47 mmol), alcohol 44 was obtained as a colorless oil (427 mg, 53% yield).

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

Procedure: According to the method of Example 26, from aldehyde 4 (294 mg, 1.16 mmol) and 1-bromohexadecane (1.42 g, 4.64 mmol), alcohol 42 was obtained as a colorless oil (283 mg, 51% yield).

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

Procedure: According to the method of Example 26, from aldehyde 4 (309 mg, 1.21 mmol) and 1-bromotetradecane (1.34 g, 4.84 mmol), alcohol 36 was obtained as a colorless oil (270 mg, 49% yield).

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

Procedure: According to the method of Example 26, from aldehyde 4 (309 mg, 1.21 mmol) and 1-bromotetradecane (1.34 g, 4.84 mmol), alcohol 36 was obtained as a colorless oil (270 mg, 49% yield).

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

Procedure: According to the method of Example 26, from aldehyde 4 (332 mg, 1.31 mmol) and 1-bromotridecane (863 mg, 3.28 mmol), alcohol 33 was obtained as a colorless oil (172 mg, 30% yield).

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

Procedure: According to the method of Example 26, from aldehyde 4 (332 mg, 1.31 mmol) and 1-bromotridecane (863 mg, 3.28 mmol), alcohol 33 was obtained as a colorless oil (172 mg, 30% yield).