Water → HCID 44287195, compound

HRID 2090381Notes

Reaction equation

HRID 2090381 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([C:12](OC)=[O:13])[NH:8][CH2:9]2)=[CH:4][CH:3]=1.[AlH4-].[Li+].O.[OH-].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([CH2:12][OH:13])[NH:8][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 28112Lithium aluminum hydrideHCID 59402378HCID 59402378, compound

Product 1

HCID 44287195HCID 44287195, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 7-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (1.0 g, 3.7 mmol) in tetrahydrofuran (20 mL) was added 1.0 M of lithium tetrahydroaluminate in tetrahydrofuran (7.40 mL, 7.40 mmol, Aldrich Cat. No. 212776) dropwise at 0° C. The solution was stirred at 0° C. for 2 h. Water (0.3 mL), 15% NaOH aqueous solution (0.3 mL) and water (1.0 mL) were added dropwise in sequence to the reaction solution. The suspension was filtered through a pad of celite, and washed with ether. The filtrate was concentrated to afford the desired compound which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=242.2.

Workup

  1. customdropwise at 0° C
  2. filtrationThe suspension was filtered through a pad of celite
  3. washwashed with ether
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-031fe1c8d20a445981a94b16a648bf93
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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