Methanol → Ethyl acetate methanol ammonium hydroxide

Participants

Reaction Steps

In a similar manner as described in Example 9 for the reaction step J, the following starting material is prepared from (3S,4R)-3-formyl-4-({isopropyl-[1-(3-methoxy-propyl)-3-methyl-1H-indole-6-carbonyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (prepared under C in example 151) (3 g, 5.4 mmol), 2N solution of methylamine in MeOH (13.5 mL, 27 mmol) and NaBH4 (0.408 g, 10.8 mmol) and purification by flash chromatography on silica gel (CH2Cl2/MeOH 90:10, then AcOEt/MeOH/NH4OH 89:10:1) to give a colorless oil. MS: 515.0 [M+H]+. ]+; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 ml/min): 5.41 min.

Provenance & Evidence