N-[4-(2-hydroxyethyl)phenyl]acetamide

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

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

Procedure: A solution of diethylazodicarboxylate (7.8 g) in DME (40 ml) was added dropwise under N2 to a stirred mixture of the product from step (a) (10.5 g), the product from step (c) (8.0 g) and triphenylphosphine (11.7 g) in DME (400 ml). When addition was complete, the mixture was stirred at room temperature for 17 hours, then evaporated in vacuo and the residue crystallised from ethanol/ether (1:4 v/v) to give the desired product as a pale yellow solid (12.7 g), [α]D25 -97.8° (c=0.50, MeOH). When addition evaporated in vacuo the residue crystallised from ethanol/ether (1:4 v/v)

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

Procedure: A solution of diethylazodicarboxylate (7.8 g) in DME (40 ml) was added dropwise under N2 to a stirred mixture of the product from step (a) (10.5 g), the product from step (c) (8.0 g) and triphenylphosphine (11.7 g) in DME (400 ml). When addition was complete, the mixture was stirred at room temperature for 17 hours, then evaporated in vacuo and the residue crystallised from ethanol/ether (1:4 v/v) to give the desired product as a pale yellow solid (12.7 g), [α]D25 -97.8° (c=0.50, MeOH). When addition evaporated in vacuo the residue crystallised from ethanol/ether (1:4 v/v)

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

Procedure: A solution of the product from step (b) (55.3 g) in methanol (250 ml) and 1N aqu. NaOH (500 ml) was stirred at room temperature for 1 hour. The methanol was evaporated in vacuo and the remaining aqueous solution adjusted to pH 4 (2N aqu. HCl), saturated with NaCl, and extracted with ethyl acetate (×3). The combined extracts were washed with water and brine, dried over MgSO4 and evaporated in vacuo to give a brown oil which was flash chromatographed through a silica column using ethyl acetate and then crystallised from ethyl acetate to give the desired product (51.7 g). The methanol was evaporated in vacuo extracted with ethyl acetate (×3) The combined extracts were washed with water and brine dried over MgSO4 evaporated in vacuo to give a brown oil which chromatographed through a silica column crystallised from ethyl acetate

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

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

Procedure: A solution of diethylazodicarboxylate (7.8 g) in DME (40 ml) was added dropwise under N2 to a stirred mixture of the product from step (a) (10.5 g), the product from step (c) (8.0 g) and triphenylphosphine (11.7 g) in DME (400 ml). When addition was complete, the mixture was stirred at room temperature for 17 hours, then evaporated in vacuo and the residue crystallised from ethanol/ether (1:4 v/v) to give the desired product as a pale yellow solid (12.7 g), [α]D25 -97.8° (c=0.50, MeOH). When addition evaporated in vacuo the residue crystallised from ethanol/ether (1:4 v/v)

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

Procedure: A solution of the product from step (b) (55.3 g) in methanol (250 ml) and 1N aqu. NaOH (500 ml) was stirred at room temperature for 1 hour. The methanol was evaporated in vacuo and the remaining aqueous solution adjusted to pH 4 (2N aqu. HCl), saturated with NaCl, and extracted with ethyl acetate (×3). The combined extracts were washed with water and brine, dried over MgSO4 and evaporated in vacuo to give a brown oil which was flash chromatographed through a silica column using ethyl acetate and then crystallised from ethyl acetate to give the desired product (51.7 g). The methanol was evaporated in vacuo extracted with ethyl acetate (×3) The combined extracts were washed with water and brine dried over MgSO4 evaporated in vacuo to give a brown oil which chromatographed through a silica column crystallised from ethyl acetate