2-((Tert-butoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acid → HCID 58398107, compound

HRID 2088983Notes

Reaction equation

HRID 2088983 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:18](O)=[O:19])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:19][CH2:18][C:12]1[CH:11]=[C:10]2[C:15]([CH2:16][CH2:17][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 189883742-((Tert-butoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 58398107HCID 58398107, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acid (0.689 g, 2.48 mmol) in THF (6 mL) at 0° C. was added LAH (4.97 mL of 1.0 M in THF, 4.97 mmol) dropwise under nitrogen. The reaction mixture was allowed to stir for 2 hours at 0° C., and then quenched with saturated aqueous ammonium chloride solution. The mixture was partitioned between water and EtOAc. The aqueous layer was extracted three times with EtOAc. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to provide tert-butyl 7-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate.

Workup

  1. customquenched with saturated aqueous ammonium chloride solution
  2. customThe mixture was partitioned between water and EtOAc
  3. extractionThe aqueous layer was extracted three times with EtOAc
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-689142755b714d2394184a683d8e7cd0
Source dataset
uspto-grants-2013_05
Patent number
US08436016B2

Reaction notes

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