Potassium Sodium Tartrate → tert-Butyl (5-(hydroxymethyl)isoquinolin-3-yl)carbamate

HRID 920251Notes

Reaction equation

HRID 920251 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:19](OC)=[O:20])[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([O-])=O.[Na+].[K+]>C1COCC1>[OH:20][CH2:19][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[CH:18]=[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[N:10]=[CH:11]2

Participants

5

Reactant 3

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

Product 1

HCID 89533802tert-Butyl (5-(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 (0.2 g, 0.662 mmol) in 6 mL THF was charged with DIBAL (3.3 mL, 3.31 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 (5-(hydroxymethyl)isoquinolin-3-yl)carbamate (26-4).

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-11db3ce0d7e54420b86b6516c0637a06
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

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