Phthalimide → HCID 67087070, compound

HRID 2365485Notes

Reaction equation

HRID 2365485 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[C:13]([O:17][C:18](=[O:29])[NH:19][C@H:20]([CH2:27]O)[CH2:21][C:22]([CH3:26])([CH3:25])[CH:23]=[CH2:24])([CH3:16])([CH3:15])[CH3:14].[C:30]1(=[O:40])[NH:34][C:33](=[O:35])[C:32]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:31]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:13]([O:17][C:18](=[O:29])[NH:19][C@H:20]([CH2:27][N:34]1[C:30](=[O:40])[C:31]2[C:32](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:33]1=[O:35])[CH2:21][C:22]([CH3:26])([CH3:25])[CH:23]=[CH2:24])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 86641904HCID 86641904, compound

Product 1

HCID 67087070HCID 67087070, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DEAD (0.63 ml, 4 mmol) is added to a suspension of ((S)-1-Hydroxymethyl-3,3-dimethyl-pent-4-enyl)-carbamic acid tert-butyl ester (1 g, 4 mmol), phthalimide (588 mg, 4 mmol) and PS-triphenylphosphine (3.72 g, 8 mmol) in THF (50 ml) and the resulting solution is stirred at room temperature overnight. The resin is removed by filtration, and the filtrate concentrated in vacuo. Purification by flash chromatography (SiO2, EtOAc/iso-hexane) yields [(S)-1-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3,3-dimethyl-pent-4-enyl]-carbamic acid tert-butyl ester as a white solid; [M+H—BOC]+ 273.

Workup

  1. customThe resin is removed by filtration
  2. concentrationthe filtrate concentrated in vacuo
  3. customPurification by flash chromatography (SiO2, EtOAc/iso-hexane)

Sources & evidence

ORD record
ord-3469ad9559134c959c635e1e70ffb4fc
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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