Phthalimide → [(R)-1-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-butyl]-carbamic acid tert-butyl ester

HRID 882884Notes

Reaction equation

HRID 882884 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[C:12]([O:16][C:17](=[O:25])[NH:18][C@@H:19]([CH2:23]O)[CH2:20][CH2:21][CH3:22])([CH3:15])([CH3:14])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl>[C:12]([O:16][C:17](=[O:25])[NH:18][C@@H:19]([CH2:23][N:5]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6])[CH2:20][CH2:21][CH3:22])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 53830465HCID 53830465, compound

Product 1

HCID 67029019[(R)-1-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-butyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of phthalimide (1.43 g, 9.72 mmol), ((R)-1-hydroxymethyl-butyl)-carbamic acid tert-butyl ester (prepared according to the procedure described in Tetrahedron Letters (1987), 28(48), 6069-72) (1.97 g, 9.69 mmol) and triphenylphosphine (2.55 g, 9.72 mmol) in DCM (25 mL) at 0° C. is added DEAD (1.6 mL, 10.2 mmol) dropwise. The reaction mixture is stirred at RT overnight. The reaction mixture is adsorbed onto silica gel and purification by column chromatography (SiO2, EtOAc/iso-hexane, gradient of 0-15% EtOAc) affords the title compound as white solid. [M+H]+ 233.

Workup

  1. customprepared
  2. customThe reaction mixture is adsorbed onto silica gel and purification by column chromatography (SiO2, EtOAc/iso-hexane, gradient of 0-15% EtOAc)

Sources & evidence

ORD record
ord-f6fe12945e5048c7bd17bb094741bb5e
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

Loading…