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

HRID 8726

Reaction equation

HRID 8726 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b8ea807d82c04522b1c9cb4cd3a35d20
Source dataset
uspto-grants-2006_08
Patent number
US07091200B2

Linked notes

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