Triphenylphosphine → HCID 23511702、化合物

HRID 354292

反応式

HRID 354292 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 23511702HCID 23511702、化合物収率 90.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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) δ1.44 (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).

後処理

  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

出典と根拠

ORDレコード
ord-05b8615f1bb84faba0c8041a89ec1abb
出典データセット
uspto-grants-2004_06
特許番号
US06756378B2

関連ノート

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