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Lithium borohydride → 1,1-Dimethylethyl 6-cyano-1-(2-hydroxyethyl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

HRID 2383314
Notes
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Reaction equation

HRID 2383314 reaction equation
C([O:5][C:6](=O)[CH2:7][CH:8]1[C:17]2[C:12](=[C:13]([CH3:20])[C:14]([C:18]#[N:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][N:9]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])CCC.[BH4-].[Li+]>C(O)C.C(OCC)C>[C:18]([C:14]1[C:13]([CH3:20])=[C:12]2[C:17](=[CH:16][CH:15]=1)[CH:8]([CH2:7][CH2:6][OH:5])[N:9]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:10][CH2:11]2)#[N:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 595910861,1-Dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-cyano-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Product 1

HCID 595910851,1-Dimethylethyl 6-cyano-1-(2-hydroxyethyl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylateYield 96.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 3283
Diethyl Ether
Solvent

Procedure

To a solution of 1,1-dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-cyano-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 18; 2.15 g, 5.56 mmol) in ethanol (10 ml) and diethyl ether (40 ml) was added lithium borohydride (2M solution in tetrahydrofuran, 4.17 ml; 8.34 mmol) at 25° C. under nitrogen. After 1.5 h at 25° C., the solvent was removed, and the residue dissolved in ethyl acetate. The solution was washed with 1N hydrochloric acid, and the aqueous layer further extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate, dried over MgSO4 and concentrated in vacuo to give the title compound (1.70 g) as a white foam.

Workup

  1. customthe solvent was removed
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe solution was washed with 1N hydrochloric acid
  4. extractionthe aqueous layer further extracted with ethyl acetate
  5. washThe combined organic phases were washed with saturated sodium bicarbonate
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-69a402ed1e9840edb9fe71de1cf2eb9b
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08263620B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes