Triethylamine → (6S)-6-[Benzyl(methyl)amino]-5,6,7,8-tetrahydronaphthalen-1-yl trifluoromethanesulfonate

HRID 420776노트

반응식

HRID 420776 반응식
[O:1](S(C(F)(F)F)(=O)=O)[S:2]([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3].[CH2:16]([N:23]([CH3:35])[C@H:24]1[CH2:33][CH2:32][C:31]2[C:30](O)=[CH:29][CH:28]=[CH:27][C:26]=2[CH2:25]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(CC)CC.[O-]S(C(F)(F)F)(=O)=O>C(Cl)Cl.CO.C(Cl)Cl>[F:6][C:5]([F:8])([F:7])[S:2]([O:1][C:30]1[C:31]2[CH2:32][CH2:33][C@H:24]([N:23]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH3:35])[CH2:25][C:26]=2[CH:27]=[CH:28][CH:29]=1)(=[O:4])=[O:3]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 2758875TrifluoromethanesulfonateHCID 59187416(6S)-6-[benzyl(methyl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol

생성물 1

HCID 59187405(6S)-6-[Benzyl(methyl)amino]-5,6,7,8-tetrahydronaphthalen-1-yl trifluoromethanesulfonate수율 24%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 21226129Dichloromethane methanol용매

실험 절차

Tf2O (3.6 mL, 21.309 mmol) was dropwise added to a −78° C. cooled solution of (6S)-6-[benzyl(methyl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol (5.30 g, 19.822 mmol) and Et3N (6 mL, 43.04 mmol) in CH2Cl2 (100 mL). Addition time: ca. 5 min. The reaction was completed after 15 min at low temperature (TLC analysis). The reaction mixture was poured into CH2Cl2 (250 mL) and washed with H2O (200 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was flash chromatographed on silica gel (1-2-3% MeOH/CH2Cl2), to furnish two batches of product: 5.78 g of pure triflate, and 1.90 g of product slightly impure (TLC analysis) (Rf=0.8 (10% MeOH/CH2Cl2), off-white solid, 73% and 24% yield).

후처리

  1. additionAddition time
  2. customca. 5 min
  3. washwashed with H2O (200 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on silica gel (1-2-3% MeOH/CH2Cl2)
  8. customto furnish two batches of product

출처 및 근거

ORD 기록
ord-23889cd77efe427dacf8a06f00d2eb72
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097641B2

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