Triethylamine → Di-tert-butyl 2-(hydroxymethyl)piperazine-1,4-dicarboxylate

HRID 1792005노트

반응식

HRID 1792005 반응식
C(N(CC)CC)C.ClC(OCC(C)C)=O.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH:24]1[C:36](O)=[O:37])=[O:22])([CH3:19])([CH3:18])[CH3:17]>O1CCCC1>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH:24]1[CH2:36][OH:37])=[O:22])([CH3:19])([CH3:18])[CH3:17]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 112559791,4-Di-Boc-piperazine-2-carboxylic acid

생성물 1

HCID 22711445Di-tert-butyl 2-(hydroxymethyl)piperazine-1,4-dicarboxylate수율 68.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Triethylamine (6.06 g) and isobutyl chloroformate (7.51 g) were added to a solution of piperazine-1,2,4-tricarboxylic acid 1,4-di-tert-butyl ester (16.52 g) in tetrahydrofuran (200 ml) at −10° C., and the mixture was stirred for 3 hours. The reaction solution was filtered, and treated with 20 ml aqueous solution of sodium borohydride (7.72 g) at −10° C. After the mixture was stirred for 1 hour, ethyl acetate (500 ml) and water (200 ml) were added thereto, and excessive sodium borohydride was quenched with 1 N hydrochloric acid. The organic layer was washed with water (200 ml), followed by saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. Then, the solvent was removed by distillation at reduced pressure. The residue was purified by silica gel column chromatography to obtain 10.87 g of the title compound from a fraction eluted with hexane-ethyl acetate (1:1).

후처리

  1. filtrationThe reaction solution was filtered
  2. additiontreated with 20 ml aqueous solution of sodium borohydride (7.72 g) at −10° C
  3. stirringAfter the mixture was stirred for 1 hour
  4. additionethyl acetate (500 ml) and water (200 ml) were added
  5. customexcessive sodium borohydride was quenched with 1 N hydrochloric acid
  6. washThe organic layer was washed with water (200 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThen, the solvent was removed by distillation at reduced pressure
  9. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-f0e7e5f9437c441f8924ef16ae231e4b
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074798B2

반응 노트

불러오는 중…