(S)-3-(tert-Butylamino)propane-1,2-diol

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

Procedure: (S)-Glycidol was added dropwise, with stirring, to a mixture of 54.7 g of tert-butylamine and 25 mL of water, heated at reflux. The resulting mixture was heated at reflux for 12 h, and was thereafter allowed to cool to room temperature. The mixture was concentrated in vacuo and was treated with ether to effect crystallization. 28.6 g (78%) of crystalline product was thus obtained: 1H NMR (CDCl3) δ1.0 (s, C(CH3)3), 2.4-2.6 (m), 3.3-4.2 (m); 13C NMR (CDCl3) δ28.6 (3 CH3), 45.2 (CH2NH), 50.2 (C(CH3)3), 65.5 (CH2OH), 70.6 (CHOH). heated at reflux The resulting mixture was heated at reflux for 12 h The mixture was concentrated in vacuo was treated with ether crystallization

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

Procedure: (S)-Glycidol was added dropwise, with stirring, to a mixture of 54.7 g of tert-butylamine and 25 mL of water, heated at reflux. The resulting mixture was heated at reflux for 12 h, and was thereafter allowed to cool to room temperature. The mixture was concentrated in vacuo and was treated with ether to effect crystallization. 28.6 g (78%) of crystalline product was thus obtained: 1H NMR (CDCl3) δ1.0 (s, C(CH3)3), 2.4-2.6 (m), 3.3-4.2 (m); 13C NMR (CDCl3) δ28.6 (3 CH3), 45.2 (CH2NH), 50.2 (C(CH3)3), 65.5 (CH2OH), 70.6 (CHOH). heated at reflux The resulting mixture was heated at reflux for 12 h The mixture was concentrated in vacuo was treated with ether crystallization

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

Procedure: (S)-Glycidol was added dropwise, with stirring, to a mixture of 54.7 g of tert-butylamine and 25 mL of water, heated at reflux. The resulting mixture was heated at reflux for 12 h, and was thereafter allowed to cool to room temperature. The mixture was concentrated in vacuo and was treated with ether to effect crystallization. 28.6 g (78%) of crystalline product was thus obtained: 1H NMR (CDCl3) δ1.0 (s, C(CH3)3), 2.4-2.6 (m), 3.3-4.2 (m); 13C NMR (CDCl3) δ28.6 (3 CH3), 45.2 (CH2NH), 50.2 (C(CH3)3), 65.5 (CH2OH), 70.6 (CHOH). heated at reflux The resulting mixture was heated at reflux for 12 h The mixture was concentrated in vacuo was treated with ether crystallization

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

Procedure: 22 g of (S)-1-tert.butylamino-2,3-dihydroxypropane, 20.7 g of benzaldehyde and 46 cc of benzene are heated at reflux in a water separator for 16 hours. The benzene and benzaldehyde are removed by distillation and the residue is distilled in a high vacuum. (S)-3-tert. butyl-5-hydroxy-methyl-2-phenyloxazolidine is obtained as yellowish oil (B.P. 110°-125° at 0.01 mm of Hg); [α]20546 = 17.8° (c = 1.99; chloroform). The benzene and benzaldehyde are removed by distillation the residue is distilled in a high vacuum

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

Procedure: 30 g of (R)-glyceraldehyde, 36 cc of tert. butylamine in 800 cc of ethanol are hydrogenated over 8 g of 10 % palladium/carbon with H2 for 4 hours, the catalyst is filtered off and the solution is concentrated. (S)-1-tert.butylamino-2,3-dihydroxy-propane is obtained from ethyl acetate/ether (2:1) in the form of crystals having a M.P. of 76°-81°. [α] 20546 = -11.8° (c = 2.0; methanol). the catalyst is filtered off the solution is concentrated