Phthalimide → HCID 58303300, compound

HRID 1896215Notes

Reaction equation

HRID 1896215 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([CH3:14])[C@H:10](O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([CH3:14])[C@@H:10]([N:20]2[C:16](=[O:26])[C:17]3[C:18](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:19]2=[O:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 5363146Diisopropyl azodicarboxylateHCID 66670433rel-1,1-Dimethylethyl (3R,4S)-3-hydroxy-4-methyl-1-piperidinecarboxylate

Product 1

HCID 58303300HCID 58303300, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of trans-3-Hydroxy-4-methyl-piperidine-1-carboxylic acid tert-butyl ester (1.78 g, 8.28 mmol) (WO 01/87838), phthalimide (1.46 g, 9.94 mmol) and TPP-resin (4.14 g) in anhydrous THF (30 ml) at 23° C. was added DIAD (2.4 ml, 12.4 mmol). The reaction mixture was stirred at 23° C. for 48 h. then the resin was filtered off and the filtrate was concentrated under reduced pressure to give an oil. The crude oil was purified by flash chromatography using silica gel (0-50% EtOAc-Heptane) which gave the title compound VIIa (1.6 g, 47% yield).

Workup

  1. filtrationthe resin was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give an oil
  4. customThe crude oil was purified by flash chromatography

Sources & evidence

ORD record
ord-3fe5037e3e774eb9b1f660e664d488e8
Source dataset
uspto-grants-2013_08
Patent number
US08518952B2

Reaction notes

Loading…