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

HRID 420776ノート

反応式

HRID 420776 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 21226129Dichloromethane methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-23889cd77efe427dacf8a06f00d2eb72
出典データセット
uspto-grants-2012_01
特許番号
US08097641B2

反応ノート

読み込み中…