1,2-Diaminocyclohexane, trans- → (S)-tert-butyl 4-(3-(2-fluoro-4-(methylsulfonyl)phenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

HRID 407880ノート

反応式

HRID 407880 の反応式
Br[C:2]1[CH:27]=[CH:26][C:5]([O:6][C@H:7]2[CH2:11][CH2:10][N:9]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[C:8]2=[O:25])=[C:4]([F:28])[CH:3]=1.[CH3:29][S:30]([O-:32])=[O:31].[Na+].[C@@H]1(N)CCCC[C@H]1N>CS(C)=O>[F:28][C:4]1[CH:3]=[C:2]([S:30]([CH3:29])(=[O:32])=[O:31])[CH:27]=[CH:26][C:5]=1[O:6][C@H:7]1[CH2:11][CH2:10][N:9]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[C:8]1=[O:25]

参加物

5

反応物 3

HCID 438061,2-Diaminocyclohexane, trans-HCID 2733271Sodium methanesulfinateHCID 86688077(S)-tert-butyl 4-(3-(4-bromo-2-fluorophenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

生成物 1

HCID 86688078(S)-tert-butyl 4-(3-(2-fluoro-4-(methylsulfonyl)phenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate収率 89.7%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

(S)-tert-Butyl 4-(3-(4-bromo-2-fluorophenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (1.8 g, 3.9 mmol) was dissolved in DMSO (30 mL) and purged with nitrogen. Sodium methanesulfinate (0.60 g, 5.9 mmol) and trans-cyclohexane-1,2-diamine (0.19 mL, 1.6 mmol) were added followed by Cu(I) triflate benzene complex (0.20 g, 0.39 mmol). The reaction was plunged into a 110° C. oil bath under nitrogen and stirred overnight. The reaction was cooled to ambient temperature, partitioned between water and EtOAc, extracted with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (100% EtOAc) to afford (S)-tert-butyl 4-(3-(2-fluoro-4-(methylsulfonyl)phenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (1.6 g, 3.5 mmol, 89% yield) as a white solid.

後処理

  1. custompurged with nitrogen
  2. customwas plunged into a 110° C.
  3. custompartitioned between water and EtOAc
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified over silica gel (100% EtOAc)

出典と根拠

ORDレコード
ord-b4e02b39efcb48069e57305ec78b7e96
出典データセット
uspto-grants-2014_06
特許番号
US08754226B2

反応ノート

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