Reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6](=[O:26])[C:7](=[C:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4]>>[CH2:3]([O:5][C:6](=[O:26])[CH:7]([CH:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:17][CH2:18]1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4]Participants
3
Procedure
To IMS (200 mL) at 0° C., NaBH4 (1.87 g, 0.047 mol) and a solution of 2-(1-(tert-butoxycarbonyl)piperidin-4-ylidene)malonic acid diethyl ester (17 g, 0.050 mol) in IMS (200 mL) were added. The resulting mixture was allowed to warm to ambient temperature and stirred for 1 h, then quenched with water and concentrated in vacuo. The resulting oil was then partitioned between EtOAc and water. The organic layer was separated and washed with brine, then dried (MgSO4) and concentrated in vacuo to afford the title compound as a yellow oil (14.6 g, 85%). LCMS (Method H): RT=3.90 min, [M+Na]+ 366.
Workup
- customquenched with water
- concentrationconcentrated in vacuo
- customThe resulting oil was then partitioned between EtOAc and water
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-a9865f61559241a29699f22d9698ecf0
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394796B2
Linked notes
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