Formic Acid → 4-Boc-3-(2-carboxy-ethyl)-morpholine

HRID 524579노트

반응식

HRID 524579 반응식
C(O)=O.C(N(CC)CC)C.[CH:11]([CH:13]1[CH2:18][O:17][CH2:16][CH2:15][N:14]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=O.[CH3:26][C:27]1(C)[O:34]C(=O)CC(=O)[O:28]1>[OH-].[Na+]>[C:22]([O:21][C:19]([N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH:13]1[CH2:11][CH2:26][C:27]([OH:34])=[O:28])=[O:20])([CH3:25])([CH3:24])[CH3:23]

참가 물질

6

반응물 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 22342783Tert-butyl 3-formylmorpholine-4-carboxylate

생성물 1

HCID 534250424-Boc-3-(2-carboxy-ethyl)-morpholine수율 40.3%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

반응 조건

온도
100 °C

실험 절차

A mixture of formic acid (2.26 mL, 58.9 mmol) and triethylamine (3.36 mL, 24.11 mmol) was stirred for 5 minutes in an ice bath. To the mixture were added tert-butyl 3-formylmorpholine-4-carboxylate (0.47 g, 2.2 mmol) and Meldrum's acid (0.32 g, 2.2 mmol) in turn at 0° C. The reaction mixture was heated at 100° C. for 5 hours, and cooled down in an ice bath. To the resulting mixture was added aqueous NaOH solution (2 mol/L, 40 mL). The aqueous layer was extracted with EtOAc (50 mL×3) and the organic layer was discarded. To the aqueous layer was added EtOAc (80 mL), and the mixture was adjusted to pH 4-5 with HCl (1 mol/L) under stirring. The aqueous layer was extracted with EtOAc (80 mL). The organic layer was dried over anhydrous Na2SO4, then filtered and the filtrate was concentrated in vacuo to give the title compound as a white solid (0.23 g, 40%). The compound was characterized by the following spectroscopic data:

후처리

  1. temperaturecooled down in an ice bath
  2. extractionThe aqueous layer was extracted with EtOAc (50 mL×3)
  3. additionTo the aqueous layer was added EtOAc (80 mL)
  4. stirringunder stirring
  5. extractionThe aqueous layer was extracted with EtOAc (80 mL)
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-5a06b252f6b54bf4ada29a6f44e92503
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340538B2

반응 노트

불러오는 중…