4-Oxo-4-(2-oxo-oxazolidin-3-yl)-butyraldehyde → 1-(cis-7-Methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-pyrrolidin-2-one

HRID 2235206Notes

Reaction equation

HRID 2235206 reaction equation
[CH3:1][C@H:2]1[C@@H:11]([NH2:12])[CH2:10][CH2:9][C:4]2([O:8][CH2:7][CH2:6][O:5]2)[CH2:3]1.[O:13]=[C:14](N1CCOC1=O)[CH2:15][CH2:16][CH:17]=O>>[CH3:1][C@H:2]1[C@@H:11]([N:12]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:13])[CH2:10][CH2:9][C:4]2([O:5][CH2:6][CH2:7][O:8]2)[CH2:3]1

Participants

3

Reactant 2

HCID 106072654-Oxo-4-(2-oxo-oxazolidin-3-yl)-butyraldehydeHCID 68468030cis-7-Methyl-1,4-dioxa-spiro[4.5]dec-8-ylamine

Product 1

HCID 684686771-(cis-7-Methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-pyrrolidin-2-oneYield 77.6%

Procedure

Using the method in Example 167 and reagents cis-7-methyl-1,4-dioxa-spiro[4.5]dec-8-ylamine (Preparation 44) (2.3 g, 13.4 mmol) and 4-oxo-4-(2-oxo-oxazolidin-3-yl)-butyraldehyde (2.3 g, 13.43 mmol) yields 2.49 g (77%) of the title compound as a white solid. 1H NMR (CDCl3) δ 4.05-4.12 (m, 1H), 3.81-3.93 (m, 4H), 3.44 (t, 2H), 2.23-2.35 (m, 3H), 1.51-1.98 (m, 8H), 0.94 (d, 3H).

Sources & evidence

ORD record
ord-db1c62b640cf4edca81af900d2f5feeb
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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