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ChemicalBook CAS DataBase List 6-(Z-AMINO)-1-HEXANOL

6-(Z-AMINO)-1-HEXANOL synthesis

11synthesis methods
-

Yield:17996-12-2 83%

Reaction Conditions:

with triethylamine in dichloromethane at 20; for 1 h;Inert atmosphere;

Steps:

26

00568] Compound 1001 - Starting compound 1000 (10 g, 85.38 mmol) was added to the reaction flask, evacuated and purged with argon. The starting material was dissolved in dichloromethane and triethylamine (23.79 rriL, 170.7 mmol) was added via syringe. N- (Benzyloxycarbonyloxy)succinimide (31.9 g, 128 mmol) was dissolved in anhydrous dichloromethane and then added to the reaction mixture via syringe. The reaction was stirred at room temperature for 1 hour. The reaction was checked by TLC (50% EtOAc/hexanes) and the reaction was concentrated under reduced pressure. The residue was dissolved in dichloromethane, added to separation funnel and organic layer was washed with 10% citric acid solution. The organic layer was separated and washed with a brine solution. The organic layer was separated and dried with sodium sulfate. The solid was filtered off and the mother liquor was concentrated. The residue was purified by flash chromatography on silica gel (10% to 100% EtOAc/hexanes) and the product fractions combined and concentrated on reduced pressure to yield 17.9g, (83%) of 1001. NMR (400 MHz, DMSO-de): δ 7.40 - 7.25 (m, 4H), 7.21 (t, J = 5.7 Hz, 1H), 4.99 (s, 2H), 4.31 (t, J = 5.1 Hz, 1H), 3.36 (m, 2H), 2.96 (q, J = 6.7 Hz, 2H), 1.38 (m, 4H), 1.32 - 1.17 (m, J = 5.2, 4.6 Hz, 4H).

References:

WO2018/136620,2018,A2 Location in patent:Paragraph 00568

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