(2S)-N-methoxy-N-methyloxolane-2-carboxamide → 1-[(2S)-tetrahydrofuran-2-yl]but-3-en-1-one

Reaction equation

CON(C)[C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][O:7]1)=[O:5].[CH3:12][C@@H:13]1C[C@H:14]1C(=O)CC=C>>[O:7]1[CH2:8][CH2:9][CH2:10][C@H:6]1[C:4](=[O:5])[CH2:14][CH:13]=[CH2:12]

Participants

Reactant 2

HCID 6712977(2S)-N-methoxy-N-methyloxolane-2-carboxamide

HCID 902534961-[(1R,2R)-2-methylcyclopropyl]but-3-en-1-one

Product 1

HCID 902384431-[(2S)-tetrahydrofuran-2-yl]but-3-en-1-one

Procedure

(2S)—N-Methoxy-N-methyltetrahydrofuran-2-carboxamide (C92) was converted to the product using the method described for the synthesis of 1-[(1R,2R)-2-methylcyclopropyl]but-3-en-1-one (C80) in Example 20. The resulting product was used in the next step without further purification. Yield: 19 g, ≦0.14 mol, ≦87%.

Workup

customThe resulting product was used in the next step without further purification

Sources & evidence

ORD record: ord-07bac94c87574982b8c0db993f8dc7dd
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403846B2

Reaction notes

Loading…