N-Hydroxyphthalimide → tert-butyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]piperidine-1-carboxylate

HRID 1821820Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[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[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1

Participants

Reactant 2

HCID 10665N-Hydroxyphthalimide

HCID 5456991-Boc-3-hydroxypiperidine

Product 1

HCID 68981003tert-butyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]piperidine-1-carboxylateYield 57%

Procedure

Reaction of tert-butyl 3-hydroxypiperidine-1-carboxylate with N-hydroxyphthalimide following the procedure described for the preparation of Reference Example 9 gave tert-butyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]piperidine-1-carboxylate (2.3 g, 57%) as a yellow oil: 1H NMR (500 MHz, CDCl3) δ 1.42 (9H, s), 1.47-1.58 (1H, m), 1.74-1.76 (1H, m), 1.90-1.92 (1H, m), 2.08-2.11 (1H, m), 3.04-3.40 (2H, m), 3.66-3.68 (1H, m), 3.70-4.14 (1H, m) 4.24-4.27 (1H, m), 7.74-7.76 (2H, m), 7.82-7.86 (2H, m).

Workup

customdescribed for the preparation of Reference Example 9

Sources & evidence

ORD record: ord-ebd65854978e452aa8cfcbc4e434de6d
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608627B2

Reaction notes

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