Tetrahydrofuran → HCID 178445732, 화합물

HRID 2389042

반응식

HRID 2389042 반응식
[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([OH:11])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].O[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([C@:23]1([CH3:29])[CH2:27][O:26][C:25](=[O:28])[NH:24]1)[CH:17]=[CH:16]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[CH2:1]([C@@H:5]1[CH2:6][CH2:7][C@H:8]([O:11][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH:19]=[C:18]([C@:23]2([CH3:29])[CH2:27][O:26][C:25](=[O:28])[NH:24]2)[CH:17]=[CH:16]3)[CH2:9][CH2:10]1)[CH2:2][CH2:3][CH3:4]

참가 물질

6

반응물 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-oneHCID 178445814HCID 178445814, 화합물

생성물 1

HCID 178445732HCID 178445732, 화합물수율 88.3%

실험 절차

A mixture of trans-4-butyl-cyclohexanol (441 mg, 2.82 mmol), ((R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one (572.5 mg, 2.353 mmol) and triphenylphosphine (741 mg, 2.82 mmol) in tetrahydrofuran (20 mL, 0.3 mol) was heated to reflux, and diisopropyl azodicarboxylate (0.556 mL, 2.82 mmol) was added dropwise. The reaction was stirred and refluxed for 3 hours. TLC and LCMS monitoring showed the reaction to be incomplete. The mixture was concentrated and taken up into dichloromethane and subjected to chromatography purification with EtOAc/hexane (10:90 to 80:20) to give product (0.793 g, 88% yield). LCMS 2.35 min (382.93, [M+1], 100%).

후처리

  1. temperatureto reflux
  2. temperaturerefluxed for 3 hours
  3. customthe reaction
  4. concentrationThe mixture was concentrated
  5. customsubjected to chromatography purification with EtOAc/hexane (10:90 to 80:20)

출처 및 근거

ORD 기록
ord-d38c3ea3fdee43ab892e5499f1056a50
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08269043B2

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