1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 54152206, 화합물

HRID 1740474노트

반응식

HRID 1740474 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@@H:9]1[CH2:14][OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][O:17][C:18]1[CH:39]=[CH:38][C:21]([C:22](Cl)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[CH:20][CH:19]=1>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@@H:9]1[CH2:14][O:15][C:22]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[C:21]1[CH:20]=[CH:19][C:18]([O:17][CH3:16])=[CH:39][CH:38]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 10680283tert-Butyl (2R,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

생성물 1

HCID 54152206HCID 54152206, 화합물수율 100%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

(2R,4R)-1-(tert-Butyloxycarbonyl)-2-hydroxymethyl-4-hydroxypyrrolidine 37 (4.4 g, 20.28 mmol) was dissolved in dry pyridine (50 ml) and allowed to stir under argon atmosphere. To this stirred solution was added TEA (2.53 g, 25 mmol) followed by 4,4'-dimethoxytrityl chloride (7.45 g, 22 mmol). The reaction mixture was stirred at room temperature for 12 h and quenched with MeOH (10 ml). The solution was evaporated to dryness and dissolved in EtOAc (200 ml). The EtOAc layer was washed with 5% NaHCO3 solution (100 ml), water (100 ml) and brine. The organic extract was dried over anhydrous Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography over silica gel using hexane→EtOAc as the eluent. The required fractions were pooled together and evaporated to give 8.09 g (100%) of an orange foam. 1HNMR (CDCl3): 1.45 (s, 9H, Boc), 1.90 (dd, 1H), 2.34 (m, 1H), 3.40-3.62 (m, 3H), 3.74 (s, 6H, 2.OCH3), 4.00 (m, 2H), 4.28 (bs, 1H), 4.44 (m, 1H), 6.82 (d, 4H, Ph), and 7.26-8.00 (m, 9H, Ph).

후처리

  1. stirringThe reaction mixture was stirred at room temperature for 12 h
  2. customquenched with MeOH (10 ml)
  3. customThe solution was evaporated to dryness
  4. dissolutiondissolved in EtOAc (200 ml)
  5. washThe EtOAc layer was washed with 5% NaHCO3 solution (100 ml), water (100 ml) and brine
  6. extractionThe organic extract
  7. dry with materialwas dried over anhydrous Na2SO4
  8. customevaporated to dryness
  9. customThe residue was purified by flash chromatography over silica gel
  10. customevaporated

출처 및 근거

ORD 기록
ord-f6f221a7097d46afb7755768d5624c9a
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05969135

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