Nitrogen → (R)-2-(1-Benzyl-cyclopropylmethyl)-succinic acid 1-methyl ester

HRID 1796135노트

반응식

HRID 1796135 반응식
[CH3:1][O:2][C:3](=[O:20])/[C:4](=[CH:9]\[C:10]1([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][CH2:11]1)/[CH2:5][C:6]([OH:8])=[O:7].C[O-].[Na+].N#N>CO>[CH3:1][O:2][C:3](=[O:20])[C@H:4]([CH2:9][C:10]1([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][CH2:12]1)[CH2:5][C:6]([OH:8])=[O:7]

참가 물질

5

반응물 3

HCID 947NitrogenHCID 10942334Sodium MethoxideHCID 696193682-[1-(1-Benzyl-cyclopropyl)-meth-(Z)-ylidene]-succinic acid 1-methyl ester

생성물 1

HCID 69619387(R)-2-(1-Benzyl-cyclopropylmethyl)-succinic acid 1-methyl ester수율 91.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 2-[1-(1-Benzyl-cyclopropyl)-meth-(Z)-ylidene]-succinic acid 1-methyl ester (2.686 g, 9.79 mmol) and sodium methoxide (0.1 eq., 0.98 mmol, 52.9 mg) in dry methanol (25 mL) was degassed with N2 for 5 min then (+)-(2S,5S)-2,5-Diethylphospholanobenzene (cyclooctadiene) Rhodium tetrafluoroborate (25 mg) was added. The mixture was hydrogenated at 60 psi for 24 hr, then concentrated in vacuum. The residue was diluted with NaHCO3 (150 mL) and the solution was made basic with NaOH and extracted with ether (80 mL). The aqueous layer was acidified to pH 1 and extracted with ether (2×100 mL). The acidic extracts were dried (MgSO4) and concentrated in vacuum to afford (R)-2-(1-Benzyl-cyclopropylmethyl)-succinic acid 1-methyl ester as a yellow oil (2.465 g, 91% yield).

후처리

  1. concentrationconcentrated in vacuum
  2. additionThe residue was diluted with NaHCO3 (150 mL)
  3. extractionextracted with ether (80 mL)
  4. extractionextracted with ether (2×100 mL)
  5. dry with materialThe acidic extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuum

출처 및 근거

ORD 기록
ord-846f0c91b56c441c8225092d441a1b48
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030116B2

반응 노트

불러오는 중…