1-Methyl-2-piperidinemethanol → Methyl(2S)-2-(tert-butoxy)-2-[(22S)-16,17-difluoro-5-(1-hydroxyethyl)-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate

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Reaction Steps

Methyl(2S)-2-(tert-butoxy)-2-[(22S)-16,17-difluoro-5-formyl-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate (0.017 g, 0.024 mmol, 1.0 equiv) and (1-methylpiperidin-2-yl)methanol (3.12 mg, 0.024 mmol, 1.0 equiv) were mixed in 1 mL toluene and concentrated to remove water. Then the mixture was re-dissolved in toluene (1.2 mL). To this solution was added 1 M dimethyl zinc (0.097 mL, 4.0 equiv) and stirred for 1 hour. It was quenched by 1 mL methanol. After concentration, the residue was used as is for the next reaction. LCMS (ESI, M+1): 720.4.

Provenance & Evidence