3a,4,5,6,7,7a-hexahydro-3H-2-benzofuran-1-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The title compound was prepared from hexahydro-isobenzofuran-l-one (10 g, 1.3 eq) and phenyl bromide (5.4 mL, 51.27 mmol) according to General Procedure K. It was obtained as a clear oil (7.40 g, 67%). HPLC Rt (5-100-8)=9.8 min. 1H NMR (CDCl3, δ): 7.4-7.2 (m, 5H), 4.05 (dd, 1H), 3.90 (dd, 1H), 2.8 (m, 1H), 2.3 (m, 1H), 2.0 (m, 1H), 1.8-1.3 (m, 6H). 13C NMR (CDCl3, δ, mult): 178.6 (0), 140.5 (0), 128.8 (1), 127.3 (1), 126.3 (1), 70.3 (2), 52.5 (0), 41.0 (1), 34.2 (2), 27.5 (2), 23.4 (2), 23.2 (2).

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The title compound was prepared from hexahydro-isobenzofuran-l-one (10 g, 1.3 eq) and phenyl bromide (5.4 mL, 51.27 mmol) according to General Procedure K. It was obtained as a clear oil (7.40 g, 67%). HPLC Rt (5-100-8)=9.8 min. 1H NMR (CDCl3, δ): 7.4-7.2 (m, 5H), 4.05 (dd, 1H), 3.90 (dd, 1H), 2.8 (m, 1H), 2.3 (m, 1H), 2.0 (m, 1H), 1.8-1.3 (m, 6H). 13C NMR (CDCl3, δ, mult): 178.6 (0), 140.5 (0), 128.8 (1), 127.3 (1), 126.3 (1), 70.3 (2), 52.5 (0), 41.0 (1), 34.2 (2), 27.5 (2), 23.4 (2), 23.2 (2).

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

Procedure: The title compound was prepared from hexahydro-isobenzofuran-l-one (10 g, 1.3 eq) and phenyl bromide (5.4 mL, 51.27 mmol) according to General Procedure K. It was obtained as a clear oil (7.40 g, 67%). HPLC Rt (5-100-8)=9.8 min. 1H NMR (CDCl3, δ): 7.4-7.2 (m, 5H), 4.05 (dd, 1H), 3.90 (dd, 1H), 2.8 (m, 1H), 2.3 (m, 1H), 2.0 (m, 1H), 1.8-1.3 (m, 6H). 13C NMR (CDCl3, δ, mult): 178.6 (0), 140.5 (0), 128.8 (1), 127.3 (1), 126.3 (1), 70.3 (2), 52.5 (0), 41.0 (1), 34.2 (2), 27.5 (2), 23.4 (2), 23.2 (2).

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:12.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At -5° C. and over a few minutes, a solution of 256 mg of ethyl chloroformate in 0.6 ml of tetrahydrofuran was added to a solution of 440 mg of the product of Step B'2 and 239 mg of triethylamine in 3.3 ml of tetrahydrofuran. The mixture was stirred for 30 minutes and then the precipitate was filtered off. The filtrate was added dropwise to a suspension of 235 mg of 95% sodium borohydride in 2.3 ml of water maintained at about 12° C. which was then left for 3 hours 30 minutes at ambient temperature. It was then cooled, acidified with 2N hydrochloric acid and extracted with methylene chloride. The extracts were dried, evaporated to dryness, purified by chromatography over silica (eluent: cyclohexane ethyl acetate, 65-35) to obtain 228 mg of (3a S, cis) hexahydro 1-(3H)-isobenzofuranone with a specific rotation of [α]D20 =-47° (c=0.6% in chloroform). At -5° C. and over a few minutes the precipitate was filtered off The filtrate was added dropwise to a suspension of 235 mg of 95% sodium borohydride in 2.3 ml of water was then left for 3 hours 30 minutes at ambient temperature It was then cooled extracted with methylene chloride The extracts were dried evaporated to dryness purified by chromatography over silica (eluent: cyclohexane ethyl acetate, 65-35)

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

Procedure: Undiluted tetrahydrophthalic acid anhydride was continuously hydrogenated in the trickle phase over 3 liters of catalyst No. 3 at a pressure of 120 bar and a temperature of 95° C. A volume/time yield of 800 g per liter of catalyst an hour was achieved. 400 Nl of exhaust gas per hour were released from the separator. The yield of hexahydrophthalic acid anhydride was 99.2%. A small amount of hexahydrophthalide was formed as by-product. a temperature of 95° C 400 Nl of exhaust gas per hour were released from the separator

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

Procedure: The title compound was prepared from hexahydro-isobenzofuran-l-one (10 g, 1.3 eq) and phenyl bromide (5.4 mL, 51.27 mmol) according to General Procedure K. It was obtained as a clear oil (7.40 g, 67%). HPLC Rt (5-100-8)=9.8 min. 1H NMR (CDCl3, δ): 7.4-7.2 (m, 5H), 4.05 (dd, 1H), 3.90 (dd, 1H), 2.8 (m, 1H), 2.3 (m, 1H), 2.0 (m, 1H), 1.8-1.3 (m, 6H). 13C NMR (CDCl3, δ, mult): 178.6 (0), 140.5 (0), 128.8 (1), 127.3 (1), 126.3 (1), 70.3 (2), 52.5 (0), 41.0 (1), 34.2 (2), 27.5 (2), 23.4 (2), 23.2 (2).