Iodine → Tert-butyl 3-(3-chloro-5-fluorophenyl)-3-hydroxypyrrolidine-1-carboxylate

HRID 1188189노트

반응식

HRID 1188189 반응식
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Cl:9])[CH:3]=1.[Mg].II.[C:13]([N:20]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>O1CCCC1>[Cl:9][C:4]1[CH:3]=[C:2]([C:22]2([OH:25])[CH2:23][CH2:24][N:20]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:21]2)[CH:7]=[C:6]([F:8])[CH:5]=1

참가 물질

6

반응물 4

HCID 807IodineHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 27362231-Bromo-3-chloro-5-fluorobenzeneHCID 5462224Magnesium

생성물 1

HCID 67402932Tert-butyl 3-(3-chloro-5-fluorophenyl)-3-hydroxypyrrolidine-1-carboxylate수율 28%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Preparation according to Preparation 1. 1-Bromo-3-chloro-5-fluorobenzene (5 g, 23.9 mmol) in dry tetrahydrofuran (100 ml), magnesium turnings (0.57 g, 23.9 mmol) and one crystal of iodine. 1-N-boc-3-pyrrolidone (4.41 g, 23.9 mmol) in dry tetrahydrofuran (50 ml). The crude product was purified by flash column chromatography on silica gel (ethyl acetate/isooctane, 1:9 to 1:1) gave the title compound (2.1 g, 28%). MS m/z (rel. intensity, 70 eV) 259 (45), 214 (69), 184 (35), 143 (37), 57 (bp).

후처리

  1. customPreparation
  2. customaccording to Preparation 1
  3. customThe crude product was purified by flash column chromatography on silica gel (ethyl acetate/isooctane, 1:9 to 1:1)

출처 및 근거

ORD 기록
ord-97727977d1d74607bf45bdfc95673297
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673962B2

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