Aluminium lithium hydride → HCID 68283976, compound

HRID 2408693Notes

Reaction equation

HRID 2408693 reaction equation
C([O:3][C:4]([C:6]1[CH:14]=[CH:13][C:12]2[N:11]([CH2:15][CH:16]([OH:23])[C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[C:10]3[CH2:24][CH2:25][NH:26][CH2:27][C:9]=3[C:8]=2[CH:7]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:3][CH2:4][C:6]1[CH:14]=[CH:13][C:12]2[N:11]([CH2:15][CH:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[OH:23])[C:10]3[CH2:24][CH2:25][NH:26][CH2:27][C:9]=3[C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68283438HCID 68283438, compound

Product 1

HCID 68283976HCID 68283976, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(2-hydroxy-2-pyridin-4-yl-ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylic acid ethyl ester (200 mg, 0.547 mmol) in dry THF (10 mL) was added portionwise LAH (63 mg, 1.65 mmol) under nitrogen at RT. After stirring for 2 h, the reaction mixture was quenched with water (0.5 mL), NaOH (1 mL). The organic layer was separated and concentrated under reduced pressure. The crude product was purified by reverse phase chromatography to yield 2-(8-hydroxymethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-1-pyridin-4-yl-ethanol. 1H NMR (CD3OD, freebase) δ (ppm): 8.41 (d, 2H), 7.42 (s, 1H), 7.39 (d, 2H), 7.3 (d, 1H), 7.19 (d, 1H), 5.08 (t, 1H), 4.66 (s, 2H), 4.4 (s, 2H), 4.3 (m, 2H), 3.5 (m, 2H), 3.2 (m, 1H), 2.9 (m, 1H). Separation by chiral HPLC provides enantiomers II-81a-b.

Workup

  1. customthe reaction mixture was quenched with water (0.5 mL), NaOH (1 mL)
  2. customThe organic layer was separated
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-a5586135cf9e412c924e739eb7e72989
Source dataset
uspto-grants-2014_08
Patent number
US08815843B2

Reaction notes

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