Potassium Sodium Tartrate → tert-Butyl (8-(hydroxymethyl)isoquinolin-3-yl)carbamate

HRID 920255Notes

Reaction equation

HRID 920255 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[N:10]=[CH:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16](C(OC)=O)[C:17]=2[CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)[C:34]([O-])=[O:35].[Na+].[K+]>C1COCC1>[OH:35][CH2:34][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[CH:11]=[N:10][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:18]2

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 89524859Methyl 3-((tert-butoxycarbonyl)amino)isoquinoline-5-carboxylate

Product 1

HCID 89533756tert-Butyl (8-(hydroxymethyl)isoquinolin-3-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 10 mL round bottom flask with methyl 3-((tert-butoxycarbonyl)amino)isoquinoline-5-carboxylate (0.473 g, 1.56 mmol) in 15 mL THF was charged with DIBAL (7.8 mL, 7.83 mmol), The reaction mixture was stirred at rt. After stirring for 2 h, the reaction mixture was added with Rochelle's salt and stirred for 1 h and then extracted with EtOAc (3×20 mL). Combined organic layer was dried, filtered and then concentrated in vacuo. Purified by silica gel chromatography (0-100% EtOAc in hexane) yielded tert-butyl (8-(hydroxymethyl)isoquinolin-3-yl)carbamate (27-4).

Workup

  1. stirringAfter stirring for 2 h
  2. stirringstirred for 1 h
  3. extractionextracted with EtOAc (3×20 mL)
  4. customCombined organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurified by silica gel chromatography (0-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-29491c1880fa4ba2af7661b81f7e93a9
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

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