Methanol → tert-Butyl hydrogen (1,5-dihydroxypentan-2-yl)carbonimidate

HRID 246130노트

반응식

HRID 246130 반응식
[BH4-].[Li+].C([O:5][C:6](=O)[C@@H:7]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][CH2:9][C:10](OCC)=[O:11])C.CO.O>C1COCC1.C(OCC)(=O)C>[C:19]([O:18][C:16](=[O:17])[NH:15][C@H:7]([CH2:6][OH:5])[CH2:8][CH2:9][CH2:10][OH:11])([CH3:22])([CH3:20])[CH3:21]

참가 물질

7

반응물 4

HCID 887MethanolHCID 962WaterHCID 4148881Lithium borohydrideHCID 14420344(S)-Diethyl 2-(tert-butoxycarbonylamino)pentanedioate

생성물 1

HCID 2734851tert-Butyl hydrogen (1,5-dihydroxypentan-2-yl)carbonimidate수율 83%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Lithium borohydride (2.0 M in THF, 4.12 ml, 8.24 mmol) was cooled in an ice bath and a solution of (S)-2-tert-butoxycarbonylamino-pentanedioic acid diethyl ester (0.5 g, 1.65 mmol) in THF (5.5 ml) was added dropwise. The reaction was warmed to room temperature and stirred 16 h. Methanol was added very slowly to the reaction mixture. After a delayed, vigorous gas evolution had subsided, water and ethyl acetate were added. The aqueous layer was extracted with ethyl acetate five times, and the combined organic layers were washed with sodium chloride solution and dried over sodium sulfate. After evaporation, the residue was purified by silica gel chromatography (methanol/dichloromethane) to give 0.3 g (83%) of ((S)-4-hydroxy-1-hydroxymethyl-butyl)-carbamic acid tert-butyl ester. (M+Na)+=242.

후처리

  1. extractionThe aqueous layer was extracted with ethyl acetate five times
  2. washthe combined organic layers were washed with sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customAfter evaporation
  5. customthe residue was purified by silica gel chromatography (methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-3126df2b95d14a2fa972e9a1c14753c6
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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