Trifluoroacetic acid → dimethyl (S)-4-(2-pyrrolidinylmethoxy)phthalate

HRID 354289ノート

反応式

HRID 354289 の反応式
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([C:25]([O:27][CH3:28])=[O:26])[C:18](=[CH:23][CH:24]=1)[C:19]([O:21][CH3:22])=[O:20])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([C:25]([O:27][CH3:28])=[O:26])[C:18](=[CH:23][CH:24]=1)[C:19]([O:21][CH3:22])=[O:20]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86587781dimethyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethoxy]phthalate

生成物 1

HCID 86595075dimethyl (S)-4-(2-pyrrolidinylmethoxy)phthalate収率 18.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of dimethyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethoxy]phthalate (5.75 g, 14.62 mmol) in CH2Cl2 (25 mL) was added TFA (20 mL), and the resulting mixture was stirred for 50 min at room temp. The resulting mixture was concentrated in vacuo and made basic with sat. NaHCO3. The mix was extracted with CH2Cl2, washed with brine, dried over MgSO4, and evaporated off in vacuo. The residue was purified by column chromatography on silica-gel with CHCl3—MeOH (50:1, v/v) as eluent to give 790 mg (18%) dimethyl (S)-4-(2-pyrrolidinylmethoxy)phthalate as a brown oil. 1H-NMR (CDCl3) δ1.48-1.57 (m, 1 H), 1.72-1.84 (m, 2 H), 1.89-1.98 (m, 2 H), 2.91-3.03 (m, 2 H), 3.48-3.54 (m, 1 H), 3.82-3.97 (m, total 8 H), 6.98 (dd, 1 H, J=2.4, 8.8 Hz), 7.06 (d, 1 H, J=2.4 Hz), 7.78 (d, 1 H, J=8.8 Hz).

後処理

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. extractionThe mix was extracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated off in vacuo
  6. customThe residue was purified by column chromatography on silica-gel with CHCl3—MeOH (50:1

出典と根拠

ORDレコード
ord-162e2812dd894409922269ef404d9bac
出典データセット
uspto-grants-2004_06
特許番号
US06756378B2

反応ノート

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