Phenylsilane → (S)-4-(2-hydroxy-2-methylpropyl)-4-phenyl-1-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-diazepan-2-one

HRID 219619노트

반응식

HRID 219619 반응식
[CH3:1][C:2](=[CH2:35])[CH2:3][C@:4]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:10][CH2:9][CH2:8][N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([B:19]3[O:23][C:22]([CH3:25])([CH3:24])[C:21]([CH3:27])([CH3:26])[O:20]3)=[CH:15][CH:14]=2)[CH3:12])[C:6](=[O:28])[NH:5]1.C1([SiH3])C=CC=CC=1.C([OH:46])(C)C.C(Cl)Cl>[Co]>[OH:46][C:2]([CH3:1])([CH3:35])[CH2:3][C@:4]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:10][CH2:9][CH2:8][N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([B:19]3[O:20][C:21]([CH3:26])([CH3:27])[C:22]([CH3:24])([CH3:25])[O:23]3)=[CH:15][CH:14]=2)[CH3:12])[C:6](=[O:28])[NH:5]1

참가 물질

5

반응물 3

HCID 12752PhenylsilaneHCID 21966342Isopropanol methylene chlorideHCID 59190370(S)-4-(2-methylallyl)-4-phenyl-1-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-diazepan-2-one

생성물 1

HCID 59190387(S)-4-(2-hydroxy-2-methylpropyl)-4-phenyl-1-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-diazepan-2-one수율 60%

시약·촉매·용매 1

HCID 104730Cobalt촉매

실험 절차

To a solution of (S)-4-(2-methylallyl)-4-phenyl-1-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-diazepan-2-one (260 mg, 0.55 mmol) in 2:1 i-propanol/CH2Cl2 (10 mL) was added cobalt catalyst A (7 mg, 2% mol) and phenylsilane (1 mL, excess). The mixture was stirred vigorously in open air for 1 h. LC-MS found the reaction completed. The mixture was quenched with 1% aq HCl, concentrated and purified by chromatography on a 12 g-silica gel cartridge, eluted with a 50˜100% EtOAc in hexanes gradient, to afford (S)-4-(2-hydroxy-2-methylpropyl)-4-phenyl-1-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-diazepan-2-one (163 mg, 60%). LC-MS Method 1 tR==2.13 min., m/z 492(M+1).

후처리

  1. customThe mixture was quenched with 1% aq HCl
  2. concentrationconcentrated
  3. custompurified by chromatography on a 12 g-silica gel cartridge
  4. washeluted with a 50˜100% EtOAc in hexanes gradient

출처 및 근거

ORD 기록
ord-02a7605e80034b999cfcd47c3926e394
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202857B2

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