N-Hydroxyphthalimide → Tert-butyl 4-(1,3-dioxoisoindolin-2-yloxy)piperidine-1-carboxylate

HRID 1821818Notes

Reaction equation

HRID 1821818 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.O[N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26]>>[O:26]=[C:17]1[C:18]2[C:19](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20](=[O:21])[N:16]1[O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 10665N-HydroxyphthalimideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 21751544Tert-butyl 4-(1,3-dioxoisoindolin-2-yloxy)piperidine-1-carboxylateYield 72%

Procedure

Reaction of tert-butyl 4-hydroxypiperidine-1-carboxylate with N-hydroxyphthalimide following the procedure described for the preparation of Reference Example 9 gave tert-butyl 4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]piperidine-1-carboxylate (3.0 g, 72%) as a yellow oil: 1H NMR (500 MHz, CDCl3) δ 1.46 (9H, s), 1.82-1.85 (2H, m), 1.92-1.96 (2H, m), 3.20-3.25 (2H, m), 3.86-3.90 (2H, m), 4.41-4.44 (1H, m), 7.74-7.78 (2H, m), 7.82-7.86 (2H, m).

Workup

  1. customdescribed for the preparation of Reference Example 9

Sources & evidence

ORD record
ord-e009b8a43c5b41b997f592cd62dc1c54
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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