Crystal structures of (R S)-N-[(1R,2S)-2-benz-yloxy-1-(2,6-di-methyl-phen-yl)prop-yl]-2-methyl-propane-2-sulfinamide and (R S)-N-[(1S,2R)-2-benz-yloxy-1-(2,4,6-tri-methyl-phen-yl)prop-yl]-2-methyl-propane-2-sulfinamide: two related protected 1,2-amino alcohols

Abstract

The title compounds, C22H31NO2S, (1), and C23H33NO2S, (2), are related protected 1,2-amino alcohols. They differ in the substituents on the benzene ring, viz. 2,6-di-methyl-phenyl in (1) and 2,4,6-tri-methyl-phenyl in (2). The plane of the phenyl ring is inclined to that of the benzene ring by 28.52 (7)° in (1) and by 44.65 (19)° in (2). In the crystal of (1), N-H⋯O=S and C-H⋯O=S hydrogen bonds link mol-ecules, forming chains along [100], while in (2), similar hydrogen bonds link mol-ecules into chains along [010]. The absolute structures of both compounds were determined by resonance scattering.

Keywords: NMR; amino alcohol; column chromatography; crystal structure; diastereomer; hydrogen bonding; sulfinamide.

Figure 1

(Top) Reaction scheme depicting the synthesis of (1) and (5) from (3a), for which (1) is the major product of the reaction. (Bottom) Reaction scheme depicting the synthesis of (6) and (7) from (3a), and (8) and (2) from (3b), for which (6) is the major product of the reaction from (3a), and (8) is the major product from (3b).

Figure 2

The mol­ecular structure of compound (1), with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Figure 3

The mol­ecular structure of compound (2), with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Figure 4

A partial view of the crystal packing of compound (1), illustrating the formation of the hydrogen-bonded chains along [100] (hydrogen bonds are shown as dashed lines; see Table 1 ▶ for details). Displacement ellipsoids are drawn at the 50% probability level.

Figure 5

A partial view of the crystal packing of compound (2), illustrating the formation of the hydrogen-bonded chains along [010] (hydrogen bonds are shown as dashed lines; see Table 2 ▶ for details). Displacement ellipsoids are drawn at the 50% probability level.