Boc-hyp-obzl

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

Procedure: t-Butyldicarbonate (1.1 g) and then sat. sodium bicarbonate (20 ml) were added to a suspension of trans-Hyp-OBn (1.1 g) in THF (25 ml) and the mixture stirred for 30 min. The mixture was diluted with ethyl acetate and washed with water, dried (MgSO4) and evaporated. Flash chromatography (SiO2 DCM then ether) gave Boc-Hyp-OBn 1.18 g. washed with water dried (MgSO4) evaporated

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

Procedure: t-Butyldicarbonate (1.1 g) and then sat. sodium bicarbonate (20 ml) were added to a suspension of trans-Hyp-OBn (1.1 g) in THF (25 ml) and the mixture stirred for 30 min. The mixture was diluted with ethyl acetate and washed with water, dried (MgSO4) and evaporated. Flash chromatography (SiO2 DCM then ether) gave Boc-Hyp-OBn 1.18 g. washed with water dried (MgSO4) evaporated

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

Procedure: t-Butyldicarbonate (1.1 g) and then sat. sodium bicarbonate (20 ml) were added to a suspension of trans-Hyp-OBn (1.1 g) in THF (25 ml) and the mixture stirred for 30 min. The mixture was diluted with ethyl acetate and washed with water, dried (MgSO4) and evaporated. Flash chromatography (SiO2 DCM then ether) gave Boc-Hyp-OBn 1.18 g. washed with water dried (MgSO4) evaporated

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

Procedure: To a solution of 10.0 g of the compound obtained in Step 157-1 in EtOAc (49 ml) was added a solution of 4 mol/L hydrochloric acid/EtOAc (39 ml). The solution was stirred at room temperature for one hour. The precipitated crystal was filtered, and the crystal was washed with EtOAc. The title compound in the amount of 6.70 g (colorless solid) was obtained. The precipitated crystal was filtered the crystal was washed with EtOAc

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (4R)-1-(tert-butoxy carbonyl)-4-hydroxy-L-proline in DMF (80 ml) was added 5.4 g of NaHCO3 and 11.1 g of benzyl bromide and the reaction mixture was stirred at 60° C. for 5 hours. Water was added to the reaction solution and the resulting mixture was extracted with EtOAc. The extract was dried over Na2SO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60; mobile phase: hexane/EtOAc=1/1 to CHCl3/MeOH=8/1; v/v) to obtain 10.0 g of the title compound (colorless oil). the resulting mixture was extracted with EtOAc The extract was dried over Na2SO4 the drying agent was separated by filtration the solvent was evaporated under reduced pressure The obtained residue was purified by column chromatography (silicagel 60; mobile phase: hexane/EtOAc=1/1 to CHCl3/MeOH=8/1; v/v)

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

Procedure: To a solution of 2-benzyl 1-tert-butyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate (565 mg) in tetrahydrofuran (10.0 mL) were added benzyl 4-hydroxybenzoate (405 mg) and 1,1′-(azodicarbonyl)dipiperidine (555 mg), and then tri-n-butyl phosphine (0.540 mL) was added thereto under ice-cooling, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 2-benzyl 1-tert-butyl (2S,4S)-4-{4-[(benzyloxy)carbonyl]phenoxy}pyrrolidine-1,2-dicarboxylate (273 mg). under ice-cooling The reaction mixture was concentrated under reduced pressure the residue was purified by silica gel column chromatography (hexane-ethyl acetate)

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

Procedure: t-Butyldicarbonate (1.1 g) and then sat. sodium bicarbonate (20 ml) were added to a suspension of trans-Hyp-OBn (1.1 g) in THF (25 ml) and the mixture stirred for 30 min. The mixture was diluted with ethyl acetate and washed with water, dried (MgSO4) and evaporated. Flash chromatography (SiO2 DCM then ether) gave Boc-Hyp-OBn 1.18 g washed with water dried (MgSO4) evaporated

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

Procedure: Morpholinosulfur trifluoride (morph-DAST; 3.5 mL, 29 mmol) was added by syringe to a solution of 1 (6.5 g, 20 mmol) in dry CH2Cl2 (200 mL) under Ar(g) at −78° C. The solution w allowed to warm to room temperature and stirred overnight. Following a quench with methanol, the reaction mixture was washed with 2×100 mL saturated NaHCO3(aq). An emulsion resulted, so the mixture was diluted with H2O and CH2Cl2 and filtered through Celite. The biphasic filtrate was separated, and the organic layer was washed with water, dried over MgSO4(s), and concentrated by rotary evaporation under reduced pressure. The resulting oil was purified by flash chromatography (1.5% v/v MeOH in CH2Cl2), which afforded 11 (3.1 g, 9.6 mmol, 48%) as a yellow oil. An additional 2.32 g of 11 that were contaminated with a minor impurity, as indicated by TLC, were also obtained from the column. a quench with methanol the reaction mixture was washed with 2×100 mL saturated NaHCO3(aq) An emulsion resulted filtered through Celite The biphasic filtrate was separated the organic layer was washed with water dried over MgSO4(s) concentrated by rotary evaporation under reduced pressure The resulting oil was purified by flash chromatography (1.5% v/v MeOH in CH2Cl2), which