Triphenylphosphine → Methyl 3-(3-(N-Boc-piperidin-4-yl)-propoxy)-phenylacetate

HRID 491544ノート

反応式

HRID 491544 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:13]([N:20]1[CH2:25][CH2:24][CH:23]([CH2:26][CH2:27][CH2:28]O)[CH2:22][CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:13]([N:20]1[CH2:21][CH2:22][CH:23]([CH2:26][CH2:27][CH2:28][O:1][C:2]2[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=2)[CH2:24][CH2:25]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 39129Methyl 3-HydroxyphenylacetateHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2800739tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylate

生成物 1

HCID 21071299Methyl 3-(3-(N-Boc-piperidin-4-yl)-propoxy)-phenylacetate収率 62%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 3-hydroxyphenylacetate (0.409 g, 2.4 mmol), 3-(N-Boc-piperidin-4-yl)-propan-1-ol (0.50 g, 20.5 mmol) and triphenylphosphine (0.645, 24.6 mmol) in THF, was added diisopropyl azodicarboxylate at 0° C. slowly, then the ice bath was removed and the reaction mixture was stirred at room temperature overnight. The solvent was removed and the residue was dissolved in methylene chloride (2 mL) and loaded on a silica gel column. The product was eluted with 20% ethyl acetate in hexane, to afford methyl 3-(3-(N-Boc-piperidin-4-yl)-propoxy)-phenylacetate (0.5 g, 62%). 1H NMR (CDCl3) δ1.1 (m, 2H), 1.4 (m, 2H), 1.46 (s, 9H), 1.66 (d, 2H), 1.78 (m, 2H), 2.67 (t, 2H), 3.58 (s, 2H), 3.68 (s, 3H), 4.05 (m, 2H), 6.75 (m, 3H), 7.18 (dd, 1H).

後処理

  1. customthe ice bath was removed
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in methylene chloride (2 mL)
  4. washThe product was eluted with 20% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-d28eae5248134eaeb9d6e2af6da6f21d
出典データセット
uspto-grants-2009_05
特許番号
US07531556B2

反応ノート

読み込み中…