1,4-Dibromobenzene → Methyl 1-(4-bromophenyl)pyrrolidine-3-carboxylate

HRID 520

반응식

HRID 520 반응식
Brc1ccc(Br)cc1.COC(=O)C1CCNC1>CC(C)(C)[O-].Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>COC(=O)C1CCN(c2ccc(Br)cc2)C1

참가 물질

7

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온도
85 °C

실험 절차

A suspension of methyl pyrrolidine-3-carboxylate (2.1 g, 16.26 mmol), 1,4-dibromobenzene (3.84 g, 16.26 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.372 g, 0.41 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.759 g, 1.22 mmol) and Sodium Tert-Butoxide (1.875 g, 19.51 mmol) in anhydrous toluene (60 mL) was stirred at 85 °C under nitrogen for 16 hours. The reaction was cooled to ambient temperature, diluted with Ether (100 mL) and filtered through celite. The filtrate was evaporated in vacuo to yield crude product. The crude product was purified by flash silica chromatography, elution gradient 5 to 20% EtOAc in heptane. Pure fractions were evaporated to dryness to afford methyl 1-(4-bromophenyl)pyrrolidine-3-carboxylate (1.460 g, 31.6 %) as a yellow solid.

출처 및 근거

ORD 기록
ord-7673f35cb6ca4307811eaa7801ce679c
출처 데이터셋
750 AstraZeneca ELN dataset
원본 링크
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