Triphenylphosphine → 4-[1-(Tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy-1-iodo-3-methylbenzene

HRID 354299

反応式

HRID 354299 の反応式
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.[C:10]([O:14][C:15]([N:17]1[CH2:23][CH2:22][CH2:21][C@H:18]1[CH2:19]O)=[O:16])([CH3:13])([CH3:12])[CH3:11].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:10]([O:14][C:15]([N:17]1[CH2:23][CH2:22][CH2:21][CH:18]1[CH2:19][O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][C:4]=1[CH3:9])=[O:16])([CH3:13])([CH3:11])[CH3:12]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 1437134-Iodo-2-methylphenolHCID 643448(S)-(-)-N-Boc-prolinolHCID 5363146Diisopropyl azodicarboxylate

生成物 1

HCID 235124474-[1-(Tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy-1-iodo-3-methylbenzene収率 78%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

To a stirred solution of 4-iodo-2-methylphenol (465 mg, 1.987 mmol), N-tert-butoxycarbonylprolinol (400 mg, 1.987 mmol), and Ph3P (625 mg, 2.384 mmol) in THF (7 mL) was added dropwise DIAD (0.5 mL, 2.404 mmol) at room temp, and the mixture was stirred for 13 hr at 70° C. The reaction mixture was concentrated in vacuo and the residue was chromatographed on silica-gel with n-hexane-EtOAc (9:1, v/v) as eluent to give 645.3 mg (78%) 4-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy-1-iodo-3-methylbenzene as a pale yellow oil. 1H-NMR (400 MHz, CDCl3) δ1.47 (s, 9H), 1.83-1.89 (m, 1H), 1.96-2.04 (m, 3H), 2.16 (s, 3H), 3.37-3.43 (br m, 2H), 3.81, 3.94 (br m each, 1H), 4.08-4.18 (m, 2H), 6.62 (br s, 1H), 7.42 (s, 2H); MS (FAB) m/z 418 (M++1).

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was chromatographed on silica-gel with n-hexane-EtOAc (9:1

出典と根拠

ORDレコード
ord-237852e4b0de4b2bba8c32fbe85e796c
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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