benzyl N-(5-bromo-2,3-dihydro-1H-inden-2-yl)carbamate → Isohexane ethyl acetate

HRID 658343ノート

反応式

HRID 658343 の反応式
[Br-].[CH2:2]([Zn+])[CH:3]([CH3:5])[CH3:4].[CH2:7]([O:14][C:15](=[O:27])[NH:16][CH:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22](Br)[CH:23]=2)[CH2:18]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:7]([O:14][C:15](=[O:27])[NH:16][C@@H:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([CH2:2][CH:3]([CH3:5])[CH3:4])[CH:23]=2)[CH2:18]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:15]([O:14][CH2:7][CH3:8])(=[O:27])[CH3:2].[CH3:11][CH2:10][CH2:9][CH:8]([CH3:13])[CH3:7]

参加物

6

反応物 2

HCID 59464189benzyl N-(5-bromo-2,3-dihydro-1H-inden-2-yl)carbamateHCID 178448254HCID 178448254、化合物

生成物 2

HCID 21882781Isohexane ethyl acetateHCID 66744187(S)-(5-Isobutyl-indan-2-yl)-carbamic acid benzyl ester

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

(S)-5-Bromo-indan-2-ylamine (1.0 g) suspended in dichloromethane (10 ml) is cooled to 0° C. and benzyl chloroformate (0.74 ml) is added dropwise and the reaction mixture is stirred for 0.5 hour. The solution is filtered to give (S)-(5-Bromo-indan-2-yl)-carbamic acid benzyl ester. PdCl2(dppf)2 (59 mg) is placed in a dry flask under argon and isobutyl zinc bromide (50 ml, 0.5 M solution in THF) is added. (5-Bromo-indan-2-yl)-carbamic acid benzyl ester (2.50 g) is dissolved in dry THF (2 ml) and the solution is added to the reaction mixture. The reaction mixture is stirred at 50° C. for 18 hours then quenched with HCl(aq) (2M) and partitioned between ethyl acetate and water. The organic layer is dried over MgSO4, filtered and the solvent removed in vacuo. The title compound is obtained by flash column chromatography (silica, eluent ethyl acetate/iso-hexane 1:4). 1H nmr (CDCl3, 400 MHz); 7.35 (m, 5H), 7.10 (d, 1H), 7.00 (s, 1H), 6.90 (d, 1H), 5.1 (s, 2H), 4.55 (m, 1H), 3.30 (m, 2H), 2.75 (dt, 2H), 2.45 (d, 2H), 1.80 (m, 1H), 0.90 (d, 6H).

後処理

  1. additionthe solution is added to the reaction mixture
  2. customthen quenched with HCl(aq) (2M)
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-972264d24c0940439c70e26c478b902a
出典データセット
uspto-grants-2011_12
特許番号
US08076489B2

反応ノート

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