Dimethylformamide → 5-(tert-Butyldimethylsilyloxymethyl)-2-(hydroxymethyl)pyridine

HRID 2183493노트

반응식

HRID 2183493 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[CH:4][N:3]=1.[Li]CCCC.CN([CH:25]=[O:26])C.[BH4-].[Na+]>CCOCC>[Si:10]([O:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:25][OH:26])=[N:3][CH:4]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 4311764Sodium borohydrideHCID 6425754Pyridine, 2-bromo-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-HCID 178418339Butyllithium

생성물 1

HCID 224732225-(tert-Butyldimethylsilyloxymethyl)-2-(hydroxymethyl)pyridine

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

The reaction was carried out as described in Example 1, Step 3 using 2-bromo-5-(tert-butyldimethylsilyloxymethyl)pyridine (12 g, 39.7 mmol), BuLi (37 ml of a 1.6 M solution in hexanes, 59.6 mmol) DMF (9.2 ml, 0.12 mol) and NaBH4 (1.5 g, 39.7 mmol) to yield, after column chromatography on silica using Et2O as eluent, the title alcohol (6.66 g, 66%).

후처리

  1. customto yield

출처 및 근거

ORD 기록
ord-e7ab6a179a474464b0422f9fdeb6c6e9
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900209B2

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