[1-(phenylmethoxymethyl)cyclopropyl]methanol

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

Procedure: 58.9 g of 1-benzyloxymethyl-1-(hydroxymethyl)cyclopropane and 88.5 g of triphenylphosphine are dissolved in 600 ml of methylene chloride, and 60 g of N-bromosuccinimide are added in portions at 0° C. The reaction mixture is stirred at room temperature for 16 h and concentrated and the residue is purified by means of FC over 3 kg of silica gel with a 1:1 mixture of methylene chloride and hexane as the eluting agent. This gives 68 g of the pure title compound: Rf (1:1 mixture from methylene chloride and hexane)=0.50. concentrated the residue is purified by means of FC over 3 kg of silica gel with a 1:1 mixture of methylene chloride and hexane as the eluting agent

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

Procedure: Methane sulfonyl chloride (5.2 mL, 68.7 mmol) was added drop wise to an ice cooled solution of {1-[(benzyloxy)methyl]cyclopropyl}methanol (Compound 63E, 11 g, 57.2 mmol) and triethylamine (15.5 mL, 114 mmol) in dichloromethane (50 mL). The reaction mixture warmed to RT and allowed to stir overnight. The reaction mixture was filtered to remove solids. The filtrate was washed with saturated sodium bicarbonate solution followed by brine, dried over magnesium sulfate, filtered and concentrated to give 12 g (77%) of the desired product as light yellow oil which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.25-7.41 (m, 5H), 4.58 (s, 2H), 4.21 (s, 2H), 3.42 (s, 2H), 2.96 (s, 3H), 0.61-0.75 (m, 4H). The reaction mixture was filtered to remove solids The filtrate was washed with saturated sodium bicarbonate solution dried over magnesium sulfate filtered concentrated

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

Procedure: Methane sulfonyl chloride (5.2 mL, 68.7 mmol) was added drop wise to an ice cooled solution of {1-[(benzyloxy)methyl]cyclopropyl}methanol (Compound 63E, 11 g, 57.2 mmol) and triethylamine (15.5 mL, 114 mmol) in dichloromethane (50 mL). The reaction mixture warmed to RT and allowed to stir overnight. The reaction mixture was filtered to remove solids. The filtrate was washed with saturated sodium bicarbonate solution followed by brine, dried over magnesium sulfate, filtered and concentrated to give 12 g (77%) of the desired product as light yellow oil which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.25-7.41 (m, 5H), 4.58 (s, 2H), 4.21 (s, 2H), 3.42 (s, 2H), 2.96 (s, 3H), 0.61-0.75 (m, 4H). The reaction mixture was filtered to remove solids The filtrate was washed with saturated sodium bicarbonate solution dried over magnesium sulfate filtered concentrated

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

Procedure: 58.9 g of 1-benzyloxymethyl-1-(hydroxymethyl)cyclopropane and 88.5 g of triphenylphosphine are dissolved in 600 ml of methylene chloride, and 60 g of N-bromosuccinimide are added in portions at 0° C. The reaction mixture is stirred at room temperature for 16 h and concentrated and the residue is purified by means of FC over 3 kg of silica gel with a 1:1 mixture of methylene chloride and hexane as the eluting agent. This gives 68 g of the pure title compound: Rf (1:1 mixture from methylene chloride and hexane)=0.50. concentrated the residue is purified by means of FC over 3 kg of silica gel with a 1:1 mixture of methylene chloride and hexane as the eluting agent