Water → 1-(Hydroxymethyl)-N-methylcyclopropanecarboxamide

Methyl 1-(methylcarbamoyl)cyclopropanecarboxylate 5b (942 mg, 6 mmol) was dissolved in 10 mL of tetrahydrofuran in a dry ice-acetone bath, by addition of a solution of diisobutylaluminum hydride in tetrahydrofuran (1 M, 18 mL), then the reaction solution was stirred for 1 h, followed by addition of 3 mL of water. After removing the dry ice-acetone bath, the reaction solution was continuously stirred at room temperature for 1 h. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure to obtain the title product 1-(hydroxymethyl)-N-methyl cyclopropanecarboxamide 5c (800 mg, a yellow solid), which was used directly in the next step.

1. customAfter removing the dry ice-acetone bath
2. stirringthe reaction solution was continuously stirred at room temperature for 1 h
3. filtrationThe reaction solution was filtered
4. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-cb177ca99b0d4589a30aa8621430d508

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388133B2