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 579523ノート

反応式

HRID 579523 の反応式
[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]

参加物

6

反応物 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

生成物 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 ester収率 50%

試薬・触媒・溶媒 3

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)触媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-d4949da2b35e4e6da5ec75f8c9a42fd6
出典データセット
uspto-grants-2015_05
特許番号
US09040703B2

反応ノート

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