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

HRID 882902Notes

Reaction equation

HRID 882902 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 13969854(S)-tert-Butyl (1-hydroxypentan-2-yl)carbamate

Product 1

HCID 66917015[(S)-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), ((S)-1-hydroxymethyl-butyl)-carbamic acid tert-butyl ester (prepared according to the procedure described in US 2007/0032433 page 232) (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 chromatograghy (SiO2, 0-15% EtOAc in iso-hexane) affords the title compound as white solid. [M+H]+ 233.

Workup

  1. customprepared
  2. customat 0° C.
  3. customThe reaction mixture is adsorbed onto silica gel and purification by chromatograghy (SiO2, 0-15% EtOAc in iso-hexane)

Sources & evidence

ORD record
ord-7c5fbf0a5aae45f7a348f1a90289c521
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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