Phthalimide → [2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

HRID 1809662Notes

Reaction equation

[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH:9](O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[C:18]1(=[O:28])[NH:22][C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH:9]([N:22]1[C:18](=[O:28])[C:19]2[C:20](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:21]1=[O:23])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 6809Phthalimide

HCID 11776Triphenylphosphine

HCID 5462977Diethyl azodicarboxylate

HCID 9816137tert-butyl N-(2-hydroxy-2-phenylethyl)carbamate

Product 1

HCID 57826431[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

Conditions

Temperature: 0 °C

Procedure

To a solution of (2-hydroxy-2-phenyl-ethyl)-carbamic acid tert-butyl ester (34.4 g, 145.0 mmol), phthalimide (21.3 g, 145 mmol), and PPh3 (49.4 g, 188.5 mmol) was added drop-wise DEAD (32.8 g, 188.5 mmol) under stirring at 0° C. After addition, the mixture was stirred at room temperature for an additional 1 hour. The mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether:ethyl acetate, 20:1 to 5:1) to give [2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester as a white solid. (Yield 39 g, 74%).

Workup

additionAfter addition
stirringthe mixture was stirred at room temperature for an additional 1 hour
concentrationThe mixture was concentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel (petroleum ether:ethyl acetate, 20:1 to 5:1)

Sources & evidence

ORD record: ord-b9b6645175734719a1e1e1b4cc45cd34
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362023B2

Reaction notes

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