3-Hydroxypyridine → 1,1-Dimethylethyl (2R)-2-[(3-pyridinyloxy)methyl]-1-pyrrolidinecarboxylate

HRID 1416591노트

반응식

HRID 1416591 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:32]([O:36][C:37]([N:39]1[CH2:43][CH2:42][CH2:41][C@@H:40]1[CH2:44][OH:45])=[O:38])([CH3:35])([CH3:34])[CH3:33].O[C:47]1[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=1>O1CCCC1>[C:32]([O:36][C:37]([N:39]1[CH2:43][CH2:42][CH2:41][C@@H:40]1[CH2:44][O:45][C:47]1[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=1)=[O:38])([CH3:35])([CH3:34])[CH3:33]

참가 물질

6

반응물 4

HCID 79713-HydroxypyridineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 688279N-(tert-Butoxycarbonyl)-D-prolinol

생성물 1

HCID 107077241,1-Dimethylethyl (2R)-2-[(3-pyridinyloxy)methyl]-1-pyrrolidinecarboxylate수율 58.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of triphenylphosphine (1.24 g, 4.74 mmol) in 20 mL of tetrahydrofuran at room temperature was added diethyl azodicarboxylate (0.746 mL, 4.74 mmol) dropwise with stirring. After stirring at room temperature for 30 minutes, (R)-1-t-butoxycarbonyl-2-pyrrolidinemethanol (350 mg, 3.16 mmol) and 3-hydroxypyridine (450 mg, 4.74 mmol) were added to the reaction mixture. The resultant solution was then stirred at room temperature overnight. After all of the starting material was consumed, the organic solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography. Elution with chloroform:methanol (10: 1) provided 518 mg of the title compound along with substantial amount of reduced DEAD reagent. MS (DCI/NH3) m/e 279 (M+H)+.

후처리

  1. stirringAfter stirring at room temperature for 30 minutes
  2. customAfter all of the starting material was consumed
  3. customthe organic solvent was evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography
  5. washElution with chloroform:methanol (10: 1)

출처 및 근거

ORD 기록
ord-123755523f814b8db24b7550ac350abc
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05914328

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