Triphenylphosphine → HCID 23511702, 화합물

HRID 350354

반응식

HRID 350354 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:13])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[C:14]([O:18][C:19]([N:21]1[CH2:27][CH2:26][CH2:25][C@H:22]1[CH2:23]O)=[O:20])([CH3:17])([CH3:16])[CH3:15].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:14]([O:18][C:19]([N:21]1[CH2:27][CH2:26][CH2:25][CH:22]1[CH2:23][O:12][C:11]1[C:2]([Cl:1])=[CH:3][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][C:10]=1[Cl:13])=[O:20])([CH3:17])([CH3:15])[CH3:16]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 76856Methyl 3,5-dichloro-4-hydroxybenzoateHCID 643448(S)-(-)-N-Boc-prolinolHCID 5363146Diisopropyl azodicarboxylate

생성물 1

HCID 23511702HCID 23511702, 화합물수율 90.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of methyl 3,5-dichloro-4-hydroxybenzoate (600 mg, 2.714 mmol), N-tert-butoxycarbonylprolinol (546 mg, 2.714 mmol), and Ph3P (854 mg, 3.257 mmol) in THF (10 mL) was added dropwise DIAD (0.68 mL, 3.283 mmol) at room temp and the mixture was stirred for 3 days at room temp, and for 18 hr at 70° C. The reaction mixture was concentrated and the residue was chromatographed on silica-gel with n-hexane-EtOAc (6:1, v/v) as eluent to give 988.8 mg (90%) methyl 4-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy-3,5-dichlorobenzoate a pale yellowish oil. 1H-NMR (400 MHz, CDCl3) δ 1.44 (s, 9H), 1.88–2.15 (br m, 3H), 2.34 (br s, 1H), 3.40–3.44 (m, 2H), 3.92 (s, 3H), 3.92, 4.14 (m, 1H), 4.18 (br s, 2H), 7.98 (s, 2H); MS (FAB) m/z 404 (M++1).

후처리

  1. waitfor 18 hr at 70° C
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was chromatographed on silica-gel with n-hexane-EtOAc (6:1

출처 및 근거

ORD 기록
ord-ce7b85c43d234ac2b7a004d452daa05e
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179819B2

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