ethyl (4R)-1,3-thiazolidine-4-carboxylate

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

Procedure: Colorless crystals of 3-[(S)-(-)-1,2,3,4-tetrahydronaphthalen-2-ylacetyl]-D-thioproline ethyl ester were prepared in the same manner as in Reference Example 1, except that (S)-(-)-1,2,3,4-tetrahydronaphthalen-2-ylacetic acid and D-thioproline ethyl ester were used instead of 2-indanyl acetic acid and L-thioproline ethyl ester, respectively (yield: 83%).

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

Procedure: A colorless oil of 1-[(R)-(+)-1,2,3,4-tetrahydronaphthalen-2-ylacetyl]-L-proline methyl ester was prepared in the same manner as in Reference Example 1, except that (R)-(+)-1,2,3,4-tetrahydronaphthalen-2-ylacetic acid and L-proline methyl ester were used instead of 2-indanyl acetic acid and L-thioproline ethyl ester, respectively (yield: 86%).

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

Procedure: A colorless oil of 1-[(R)-(+)-1,2,3,4-tetrahydronaphthalen-2-ylacetyl]-L-proline methyl ester was prepared in the same manner as in Reference Example 1, except that (R)-(+)-1,2,3,4-tetrahydronaphthalen-2-ylacetic acid and L-proline methyl ester were used instead of 2-indanyl acetic acid and L-thioproline ethyl ester, respectively (yield: 86%).

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

Procedure: Colorless crystals of 1-[(S)-(-)-1,2,3,4-tetrahydronaphthalen-2-ylacetyl]-L-proline methyl ester were prepared in the same manner as in Reference Example 1, except that (S)-(-)-1,2,3,4-tetrahydronaphthalen-2-ylacetic acid and L-proline methyl ester were used instead of 2-indanyl acetic acid and L-thioproline ethyl ester, respectively yield: 72%).

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

Procedure: To a mixture of 2.85 g of 1,2,3,4-tetrahydronaphthalen-2-ylacetic acid and 13.45 g of WSC.HCl was added 45 ml of methylene chloride under ice-cooling. The mixture was stirred for 5 minutes at room temperature. To this was added a solution of 2.4 g of L-thioproline ethyl ester in 7 ml of methylene chloride at room temperature, and the mixture was stirred for a further 18 hours at the same temperature. The reaction mixture was washed with water, diluted hydrochloric acid, and saturated sodium hydrogen carbonate in this order. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography to produce 3.4 g of 3-(1,2,3,4-tetrahydronaphthalen-2-ylacetyl)-L-thioproline ethyl ester as a colorless oil (yield: 68%). cooling the mixture was stirred for a further 18 hours at the same temperature The reaction mixture was washed with water, diluted hydrochloric acid, and saturated sodium hydrogen carbonate in this order The organic layer was dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure The residue thus obtained was purified by silica gel column chromatography

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

Procedure: 1.4 g of 2-indanylacetic acid and 1.9 g of WSC.HCl were added to 15 ml of methylene chloride under ice-cooling. The mixture was stirred for 5 minutes at room temperature. After an addition of 1.3 g of L-thioproline ethyl ester dissolved in 10 ml of methylene chloride, the mixture was stirred for 5 hours. The reaction mixture was washed with water, diluted hydrochloric acid, and saturated sodium hydrogen carbonate in this order. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography to produce 1.45 g of 3-(2-indanylacetyl)-L-thioproline ethyl ester as a colorless oil (yield: 57%). cooling the mixture was stirred for 5 hours The reaction mixture was washed with water, diluted hydrochloric acid, and saturated sodium hydrogen carbonate in this order The organic layer was dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure The residue thus obtained was purified by silica gel column chromatography

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

Procedure: While chilling with ice water, 1.4 g of 2-indanyl-acetic acid and 1.9 g of WSC.HCl were added to 15 ml of methylene chloride, and the mixture was stirred at room temperature for 5 minutes. Then, 1.3 g of L-thioproline ethyl ester dissolved in 10 ml of methylene chloride were added at room temperature, and the mixture was stirred further for 5 hours. The resultant liquid reaction mixture was washed with water, diluted hydrochloric acid and a saturated aqueous solution of sodium bicarbonate in that order. After an organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resultant residue was subjected to column chromatography on silica gel, thereby obtaining 1.45 g (57%) of 3-(2-indanylacetyl)-L-thioproline ethyl ester in the form of colorless oil. were added at room temperature the mixture was stirred further for 5 hours The resultant liquid reaction mixture was washed with water, diluted hydrochloric acid After an organic layer was dried over anhydrous magnesium sulfate the solvent was distilled off under reduced pressure

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

Procedure: While chilling with ice water, 1.4 g of 2-indanyl-acetic acid and 1.9 g of WSC.HCl were added to 15 ml of methylene chloride, and the mixture was stirred at room temperature for 5 minutes. Then, 1.3 g of L-thioproline ethyl ester dissolved in 10 ml of methylene chloride were added at room temperature, and the mixture was stirred further for 5 hours. The resultant liquid reaction mixture was washed with water, diluted hydrochloric acid and a saturated aqueous solution of sodium bicarbonate in that order. After an organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resultant residue was subjected to column chromatography on silica gel, thereby obtaining 1.45 g (57%) of 3-(2-indanylacetyl)-L-thioproline ethyl ester in the form of colorless oil. were added at room temperature the mixture was stirred further for 5 hours The resultant liquid reaction mixture was washed with water, diluted hydrochloric acid After an organic layer was dried over anhydrous magnesium sulfate the solvent was distilled off under reduced pressure

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

Procedure: Colorless crystals of 3-[(S)-(-)-1,2,3,4-tetrahydronaphthalen-2-ylacetyl]-D-thioproline ethyl ester were prepared in the same manner as in Reference Example 1, except that (S)-(-)-1,2,3,4-tetrahydronaphthalen-2-ylacetic acid and D-thioproline ethyl ester were used instead of 2-indanyl acetic acid and L-thioproline ethyl ester, respectively (yield: 83%).

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

Procedure: A colorless oil of 1-[(R)-(+)-1,2,3,4-tetrahydronaphthalen-2-ylacetyl]-L-proline methyl ester was prepared in the same manner as in Reference Example 1, except that (R)-(+)-1,2,3,4-tetrahydronaphthalen-2-ylacetic acid and L-proline methyl ester were used instead of 2-indanyl acetic acid and L-thioproline ethyl ester, respectively (yield: 86%).

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

Procedure: Colorless crystals of 1-[(S)-(-)-1,2,3,4-tetrahydronaphthalen-2-ylacetyl]-L-proline methyl ester were prepared in the same manner as in Reference Example 1, except that (S)-(-)-1,2,3,4-tetrahydronaphthalen-2-ylacetic acid and L-proline methyl ester were used instead of 2-indanyl acetic acid and L-thioproline ethyl ester, respectively yield: 72%).

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

Procedure: To a mixture of 2.85 g of 1,2,3,4-tetrahydronaphthalen-2-ylacetic acid and 13.45 g of WSC.HCl was added 45 ml of methylene chloride under ice-cooling. The mixture was stirred for 5 minutes at room temperature. To this was added a solution of 2.4 g of L-thioproline ethyl ester in 7 ml of methylene chloride at room temperature, and the mixture was stirred for a further 18 hours at the same temperature. The reaction mixture was washed with water, diluted hydrochloric acid, and saturated sodium hydrogen carbonate in this order. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography to produce 3.4 g of 3-(1,2,3,4-tetrahydronaphthalen-2-ylacetyl)-L-thioproline ethyl ester as a colorless oil (yield: 68%). cooling the mixture was stirred for a further 18 hours at the same temperature The reaction mixture was washed with water, diluted hydrochloric acid, and saturated sodium hydrogen carbonate in this order The organic layer was dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure The residue thus obtained was purified by silica gel column chromatography