Trityl chloride → (s)-2-(Tritylamino)butan-1-ol

HRID 81423노트

반응식

HRID 81423 반응식
[NH2:1][C@@H:2]([CH2:5][CH3:6])[CH2:3][OH:4].CCN(C(C)C)C(C)C.[C:16](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCCCCC>C(Cl)Cl.CO.CCOCC>[C:16]([NH:1][C@@H:2]([CH2:5][CH3:6])[CH2:3][OH:4])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

참가 물질

8

반응물 4

HCID 6456Trityl chlorideHCID 8058HexaneHCID 81531DiisopropylethylamineHCID 1200842-Amino-1-butanol, (+)-

생성물 1

HCID 57433108(s)-2-(Tritylamino)butan-1-ol

시약·촉매·용매 3

HCID 887Methanol용매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of (S)-(+)-2-aminobutan-1-ol (10 g, 1 eq, 112.18 mmol) in DCM (500 mL) under an argon atmosphere at room temperature, was added DIEA (30 mL, 1.54 eq, 172.22 mmol) followed by trityl chloride (35.4 mL, 1.13 eq, 126.98 mmol). The reaction mixture was stirred at this temperature for 48 h, when TLC (hexane:ether:MeOH; 55:40:5) indicated that the reaction had gone to completion. The solvent was evaporated in vacuo and the residue precipitated from acetone (50 mL) with hexane (900 mL) with stirring, the precipitate was removed by filtration and the filtrate was evaporated in vacuo. The residue was dissolved in hexane (1 L), filtered, and the filtrate was evaporated in vacuo to afford the title compound as a light yellow oil. Yield: 33 g (89%). 1H-NMR (d6-DMSO, 250 MHz): δ 0.58 (t, 3H, J=7.26 Hz, —NHCH(CH2CH3)CH2OH), 1.10 (m, 2H, —NHCH(CH2CH3)CH2OH), 2.24 (m, 1H, —NHCH(CH2CH3)CH2OH), 2.39 (m, 1H, —NHCH(CH2CH3)CH2OH), 2.76 & 3.03 (2×m, 2H, —NHCH(CH2CH3)CH2OH), 4.32 (t, 1H, J=4.97 Hz, —NHCH(CH2CH3)CH2OH), 7.15-7.52 (m, 15H, 3×Ph).

후처리

  1. customThe solvent was evaporated in vacuo
  2. customthe residue precipitated from acetone (50 mL) with hexane (900 mL)
  3. stirringwith stirring
  4. customthe precipitate was removed by filtration
  5. customthe filtrate was evaporated in vacuo
  6. dissolutionThe residue was dissolved in hexane (1 L)
  7. filtrationfiltered
  8. customthe filtrate was evaporated in vacuo

출처 및 근거

ORD 기록
ord-dd494d617f7f4aedba107272bac72029
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846696B2

반응 노트

불러오는 중…