Triphenylphosphine → dimethyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethoxy]phthalate

HRID 354288

반응식

HRID 354288 반응식
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].[C:16]([N:23]1[CH2:29][CH2:28][CH2:27][C@H:24]1[CH2:25]O)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:19]([O:18][C:16]([N:23]1[CH2:29][CH2:28][CH2:27][C@H:24]1[CH2:25][O:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:17])([CH3:22])([CH3:20])[CH3:21]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 89726Dimethyl 4-hydroxyphthalateHCID 643448(S)-(-)-N-Boc-prolinolHCID 5363146Diisopropyl azodicarboxylate

생성물 1

HCID 86587781dimethyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethoxy]phthalate수율 102.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of dimethyl 4-hydroxyphthalate (3.00 g, 14.27 mmol), N-Boc-prolinol (2.87 g, 14.26 mmol), Ph3P (4.49 g, 17.12 mmol) in THF (50 mL) was added DIAD (3.40 mL, 17.27 mmol) at 0° C. Then the resulting mixture was heated under reflux overnight. The resulting mixture was evaporated and the residue was purified by column chromatography on silica-gel with n-hexane-EtOAc (3:1, v/v) as eluent to give 5.75 g (q.y.) dimethyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl methoxy]phthalate as an oil. 1H-NMR (CDCl3) δ1.47 (s, 9 H), 1.86-2.05 (m, 4 H), 3.36-3.40 (m, 2 H), 3.87 (m, 3 H), 3.91 (s, 3 H), 3.96-4.19 (m, 3 H), 7.03-7.24 (m, 2 H), 7.80 (m, 1H).

후처리

  1. temperatureThen the resulting mixture was heated
  2. temperatureunder reflux overnight
  3. customThe resulting mixture was evaporated
  4. customthe residue was purified by column chromatography on silica-gel with n-hexane-EtOAc (3:1

출처 및 근거

ORD 기록
ord-bb8d47fb26aa4ab0a3a5ddf97102a060
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

연결된 노트

불러오는 중…