ChemicalBook CAS DataBase List 3-(dibenzylamino)-2,2-difluoropropan-1-ol

3-(dibenzylamino)-2,2-difluoropropan-1-ol synthesis

4synthesis methods

Product Name:3-(dibenzylamino)-2,2-difluoropropan-1-ol
CAS Number:890147-32-7
Molecular formula:C17H19F2NO
Molecular Weight:291.34

541547-36-8 Synthesis

ethyl 3-(dibenzylaMino)-2,2-difluoropropanoate

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3-(dibenzylamino)-2,2-difluoropropan-1-ol

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Yield:890147-32-7 80%

Reaction Conditions:

Stage #1: ethyl N,N-(dibenzyl)-2,2-difluoro-3,3-aminopropanoatewith diisobutylaluminium hydride in tetrahydrofuran;hexane at -78 - 20; for 18 h;
Stage #2: with sodium hydroxide in tetrahydrofuran;hexane;water;

Steps:

1090.76

At -78° C. to a solution of ethyl 3-(dibenzylamino)-2,2-difluoropropanoate (1.19 g, 3.5 mmol) in THF (20 mL) was added DIBAL-H (15 mL, 1.0 M in hexane, 15 mmol) dropwise. The temperature was maintained at below -70° C. during the addition. After the addition, the acetone-dry ice bath was removed and the reaction mixture was allowed to warm up to room temperature and stirred for 18 h. Celite was added to the reaction mixture, followed by the slow addition of H₂O (5 mL), 2 N NaOH (5 mL) and H₂O (5 mL). The reaction mixture was filtered, concentrated in vacuo and purified by ISCO chromatography to give 3-(dibenzylamino)-2,2-difluoropropan-1-ol as a colorless oil (810 mg, 80% yield) LCMS: RT=2.48 min [M+H] 292.15 (LCMS Method 1).

References:

US2007/161685,2007,A1 Location in patent:Page/Page column 461

Propanoic acid, 3-[bis(phenylmethyl)amino]-2,2-difluoro-, methyl ester

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References

103-49-1 Synthesis

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References

N-((1H-benzo[d][1,2,3]triazol-1-yl)Methyl)-N-benzyl-1-phenylMethanaMine

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References