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

HRID 491544노트

반응식

HRID 491544 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d28eae5248134eaeb9d6e2af6da6f21d
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531556B2

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