Triphenylphosphine → (R)-di-tert-butyl 1-((tetrahydrofuran-2-yl)methyl)hydrazine-1,2-dicarboxylate

HRID 536701노트

반응식

HRID 536701 반응식
[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6]O.[NH:8]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OC(C)(C)C)=O)=N\C(OC(C)(C)C)=O>C1COCC1>[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][N:8]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[NH:9][C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 85431Di-tert-butyl bicarbamateHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 6931745(2R)-oxolan-2-ylmethanol

생성물 1

HCID 66643239(R)-di-tert-butyl 1-((tetrahydrofuran-2-yl)methyl)hydrazine-1,2-dicarboxylate수율 95.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of (R)-(tetrahydrofuran-2-yl)methanol (Fluka, 4.0 g, 39.2 mmol) and di-tert-butyl hydrazine-1,2-dicarboxylate (9.1 g, 39.2 mmol) in THF (50 mL) was added triphenylphosphine (14.4 g, 54.8 mmol) followed by (E)-di-tert-butyl diazene-1,2-dicarboxylate (12.6 g, 54.8 mmol), portionwise. This mixture was stirred at ambient temperature for 16 h then was concentrated under reduced pressure and purified by column chromatography (SiO2, 99% hexane/EtOAc to 25% hexane/EtOAc) to give the title compound (11.8 g, 37.3 mmol, 95% yield). MS (DCI/NH3) m/z 317 (M+H)+.

후처리

  1. concentrationthen was concentrated under reduced pressure
  2. custompurified by column chromatography (SiO2, 99% hexane/EtOAc to 25% hexane/EtOAc)

출처 및 근거

ORD 기록
ord-56053afbf4b346cca1ddc89819ea8f76
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859596B2

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