Water → cis-4-(4-Bromophenoxy)tetrahydrofuran-3-amine

HRID 2060828노트

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HRID 2060828 반응식
[N:1]([C@H:4]1[C@@H:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=2)[CH2:7][O:6][CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C@H:8]2[CH2:7][O:6][CH2:5][C@H:4]2[NH2:1])=[CH:11][CH:12]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86653048cis-3-Azido-4-(4-bromophenoxy)tetrahydrofuran

생성물 1

HCID 67193588cis-4-(4-Bromophenoxy)tetrahydrofuran-3-amine수율 59.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of cis-3-azido-4-(4-bromophenoxy)tetrahydrofuran (286.7 g, 1.01 mol) in tetrahydrofuran (1.25 L) was cooled to 0° C. and treated with triphenylphosphine (278 g, 1.06 mol). The reaction was allowed to warm to room temperature and stirred for 18 hours. Water (53 mL) was added and the reaction was stirred at room temperature for 66 hours. Solvent was removed under reduced pressure and the residue was mixed with diethyl ether. The supernatant was decanted and concentrated in vacuo, providing a residue, which was filtered through a short plug of silica gel (Gradient: 0% to 5% methanol in methylene chloride) to afford cis-4-(4-bromophenoxy)tetrahydrofuran-3-amine (155 g) and 366 grams of impure product. An acid/base extraction was carried out on the impure material, providing additional product (48.5 g). Total yield: 203.5 g, 0.788 mol, 68% over four steps. 1H NMR (300 MHz, CDCl3) δ 3.6 (m, 1H), 3.7 (m, 1H), 3.9 (m, 1H), 4.0 (m, 1H), 4.1 (m, 1H), 4.6 (m, 1H), 6.8 (m, 2H), 7.3 (m, 2H).

후처리

  1. stirringthe reaction was stirred at room temperature for 66 hours
  2. customSolvent was removed under reduced pressure
  3. additionthe residue was mixed with diethyl ether
  4. customThe supernatant was decanted
  5. concentrationconcentrated in vacuo
  6. customproviding a residue, which
  7. filtrationwas filtered through a short plug of silica gel (Gradient: 0% to 5% methanol in methylene chloride)

출처 및 근거

ORD 기록
ord-e39d0177cd184026aaa27e95dcacd761
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278457B2

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