2-(Di-tert-butylphosphino)biphenyl → (S)-1-{4-[3-(4-Ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethylamine

HRID 40507노트

반응식

HRID 40507 반응식
[CH2:1]([O:3][C:4]1[CH:14]=[CH:13][C:7]([O:8][CH:9]2[CH2:12][NH:11][CH2:10]2)=[CH:6][CH:5]=1)[CH3:2].C(OC(=O)[NH:21][C@H:22]([C:24]1[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=1)[CH3:23])(C)(C)C.CC([O-])(C)C.[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>O1CCOCC1.O.CO>[CH2:1]([O:3][C:4]1[CH:14]=[CH:13][C:7]([O:8][CH:9]2[CH2:12][N:11]([C:27]3[CH:28]=[CH:29][C:24]([C@@H:22]([NH2:21])[CH3:23])=[CH:25][CH:26]=3)[CH2:10]2)=[CH:6][CH:5]=1)[CH3:2]

참가 물질

8

반응물 4

HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23665647Potassium tert-butoxideHCID 534093113-(4-Ethoxyphenoxy)azetidineHCID 56973617(S)-tert-Butyl (1-(4-bromophenyl)ethyl)carbamate

생성물 1

HCID 86689010(S)-1-{4-[3-(4-Ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethylamine

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
120 °C

실험 절차

To 5.0 g (21.8 mmol) 3-(4-ethoxy-phenoxy)-azetidine and 6.5 g (21.8 mmol) (S)-[1-(4-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (1.3) in 80 mL 1,4-dioxane under an argon atmosphere are added 8.6 g (87.1 mmol) KOtBu, 0.65 g (2.18 mmol) 2-(di-tert-butylphosphino)biphenyl and 1.0 g (1.09 mmol) tris-(dibenzylideneacetone)-dipalladium(0). The mixture is stirred for 2 h at 120° C. Subsequently 200 mL MeOH and 5 mL water are added and the mixture is filtered and concentrated in vacuo. The residue is taken up in ethyl acetate and is washed with water. The organic layer is concentrated and the residue is purified by HPLC (eluent A: water+0.1% NH4OH, eluent B: MeOH) to yield the desired product.

후처리

  1. filtrationthe mixture is filtered
  2. concentrationconcentrated in vacuo
  3. washis washed with water
  4. concentrationThe organic layer is concentrated
  5. customthe residue is purified by HPLC (eluent A: water+0.1% NH4OH, eluent B: MeOH)

출처 및 근거

ORD 기록
ord-fdb4a14c01f14561a6767d063c044631
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530461B2

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