Aluminium lithium hydride → HCID 68283976, compound

HRID 1469529Notes

Reaction equation

HRID 1469529 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-0a64ecfd39e04714b613280d72449e29
Source dataset
uspto-grants-2015_04
Patent number
US09006263B2

Reaction notes

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