4,4,5,5-Tetramethyl[1,3,2]dioxaborolane → 5-Ethyl-2,2-diphenyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-butyl]-oxazolidine-4-carboxylic acid tert-butyl ester

HRID 579523노트

반응식

HRID 579523 반응식
[C:1]([O:5][C:6]([C:8]1([CH2:27][CH2:28][CH:29]=[CH2:30])[CH:12]([CH2:13][CH3:14])[O:11][C:10]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:31][C:32]1([CH3:39])[C:36]([CH3:38])([CH3:37])[O:35][BH:34][O:33]1>ClCCl.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[C:1]([O:5][C:6]([C:8]1([CH2:27][CH2:28][CH2:29][CH2:30][B:34]2[O:35][C:36]([CH3:38])([CH3:37])[C:32]([CH3:39])([CH3:31])[O:33]2)[CH:12]([CH2:13][CH3:14])[O:11][C:10]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 2

HCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 668332184-But-3-enyl-5-ethyl-2,2-diphenyl-oxazolidine-4-carboxylic acid tert-butyl ester

생성물 1

HCID 668332165-Ethyl-2,2-diphenyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-butyl]-oxazolidine-4-carboxylic acid tert-butyl ester수율 50%

시약·촉매·용매 3

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4-but-3-enyl-5-ethyl-2,2-diphenyl-oxazolidine-4-carboxylic acid tert-butyl ester (230 mg, 0.56 mmol) in dichloromethane (2 mL, 0.3 M) was added chlorotris (triphenylphosphine)rhodium(I) (60 mg, 0.065 mmol, 10 mol %) at room temperature. After stirring for 30 min, 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane (200 μl, 1.3 mmol, 2 eq) was added to the reaction mixture and stirred overnight. After quenching the reaction with water (3 mL), the resulting solution was diluted with ethyl acetate and washed successively with water and saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. Purification by MPLC (1-40% ethyl acetate in heptane) gave 5-Ethyl-2,2-diphenyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-butyl]-oxazolidine-4-carboxylic acid tert-butyl ester (152 mg, 0.28 mmol, 50%).

후처리

  1. stirringstirred overnight
  2. customAfter quenching
  3. customthe reaction with water (3 mL)
  4. washwashed successively with water and saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by MPLC (1-40% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-d4949da2b35e4e6da5ec75f8c9a42fd6
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040703B2

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