Water → 1,1-Dimethylethyl 3,4-dihydro-5-(hydroxymethyl)-2(1H)-isoquinolinecarboxylate

HRID 8726

반응식

HRID 8726 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[CH:18]=[O:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O.[Cl-].[NH4+]>CO.O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[CH2:18][OH:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 22335239Tert-butyl 5-formyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

생성물 1

HCID 695612161,1-Dimethylethyl 3,4-dihydro-5-(hydroxymethyl)-2(1H)-isoquinolinecarboxylate수율 68.8%

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

To solution of 5-formyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 20a (0.44 g, 1.71 mmol) in 40 mL of methanol:tetrahydrofuran (1:1) at room temperature was added sodium borohydride (0.072 g, 1.88 mmol), and the mixture was stirred to room temperature for 3 h. Water (30 mL) was added followed by ammonium chloride saturated solution (20 mL) and the product was extracted with dichloromethane. The combined organics were dried over magnesium sulfate, the solvent was evaporated and the residue was purified by flash chromatography eluting with 30% ethyl acetate in hexanes, to yield 0.31 g of 5-hydroxymethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 21a.

후처리

  1. extractionthe product was extracted with dichloromethane
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. customthe solvent was evaporated
  4. customthe residue was purified by flash chromatography
  5. washeluting with 30% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-b8ea807d82c04522b1c9cb4cd3a35d20
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091200B2

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