1,4-Dioxane hydrochloride → 2-[(2S)-2-amino-3-cyclohexylpropyl]-1H-isoindole-1,3(2H)-dione

HRID 340003Notes

Reaction equation

HRID 340003 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:21]C(=O)OC(C)(C)C)[CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCOCC1.Cl>C1COCC1>[NH2:21][C@@H:8]([CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:9][N:10]1[C:11](=[O:20])[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]1=[O:19]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 57544826tert-butyl {(1S)-2-cyclohexyl-1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]ethyl}carbamate

Product 1

HCID 670661172-[(2S)-2-amino-3-cyclohexylpropyl]-1H-isoindole-1,3(2H)-dioneYield 110.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl {(1S)-2-cyclohexyl-1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]ethyl}carbamate (2.8 g, 7.25 mmol) in 4 M HCl dioxane (10 mL, 40 mmol) and THF (10 mL) was stirred at room temperature for 2 hours. The reaction mixture was evaporated under reduced pressure to afford 2.3 g (99% yield) of the desired product. LC-MS found: 287.1 (M+H)+.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ee592338419f4789b9139dc331fdcbda
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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