Triethylamine → 1-(1,4-Dioxaspiro[4.5]decan-8-yl)pyrrolidin-2-one

HRID 1013788

반응식

HRID 1013788 반응식
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.Cl.C[O:14][C:15](=O)[CH2:16][CH2:17][CH2:18][NH2:19].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([N:19]3[CH2:18][CH2:17][CH2:16][C:15]3=[O:14])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 27563834-Aminobutyric acid methyl ester hydrochlorideHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 109002931-(1,4-Dioxaspiro[4.5]decan-8-yl)pyrrolidin-2-one수율 50.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Dissolve 1,4-dioxaspiro{4.5}decan-8-one (100 g, 640.3 mmol), methyl-4-aminobutyrate hydrochloride (98.5 g, 640.3 mmol), triethylamine (90 mL, 640.3 mmol) and dichloromethane (2 L) and stir at room temperature. Add Sodium triacetoxyborohydride (135.7 g, 640.3 mmol) stir 17 h at room temperature. Quench with water (1 L), separate, wash the aqueous layer with dichloromethane (3×500 mL), combine the organic phases and dry over anhydrous sodium sulfate, filter and concentrate. Purify the material on a 1.5 kg silica column, 6 inches in diameter, and eluted with 8:2 hexanes/ethyl acetate to 95:5 ethyl acetate/methanol to give 73 g of the title compound as a waxy brown solid. 1H NMR (CDCl3) δ 3.99-4.10 (m, 1H), 3.93 (s, 4H), 3.32-3.36 (m, 2H), 2.36-2.40 (m, 2H), 1.94-2.03 (m, 2H), 1.65-1.83 (m, 8H).

후처리

  1. customQuench with water (1 L)
  2. customseparate
  3. washwash the aqueous layer with dichloromethane (3×500 mL)
  4. dry with materialdry over anhydrous sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the material on a 1.5 kg silica column, 6 inches in diameter
  8. washeluted with 8:2 hexanes/ethyl acetate to 95:5 ethyl acetate/methanol

출처 및 근거

ORD 기록
ord-557e919ea30e4768977f875f741c8d7a
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981918B2

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