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

HRID 658343노트

반응식

HRID 658343 반응식
[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]

참가 물질

6

반응물 2

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

생성물 2

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

시약·촉매·용매 2

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

반응 조건

온도
50 °C

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-972264d24c0940439c70e26c478b902a
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076489B2

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