Sodium Hydroxide → HCID 58101268, compound

HRID 237322Notes

Reaction equation

HRID 237322 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([CH:18]3[C:30]4[N:29]([CH2:31][C:32]#[N:33])[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[C:22]=4[CH2:21][CH2:20][N:19]3[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1.[OH-].[Na+]>C(OCC)C>[NH2:33][CH2:32][CH2:31][N:29]1[C:30]2[CH:18]([C:14]3([C:11]4[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][CH:12]=4)[CH2:15][CH2:16][CH2:17]3)[N:19]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:20][CH2:21][C:22]=2[C:23]2[C:28]1=[CH:27][CH:26]=[CH:25][CH:24]=2

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 21226445Aluminium lithium hydrideHCID 58101298HCID 58101298, compound

Product 1

HCID 58101268HCID 58101268, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-5 °C

Procedure

Lithium aluminium hydride (0.281 g, 7.41 mmol) was suspended in diethyl ether (40 mL). The slurry was cooled to −5° C. and tert-butyl 1-[1-(4-chlorophenyl)cyclobutyl]-9-(cyanomethyl)-1,3,4,9-tetrahydro-2H-b-carboline-2-carboxylate (2.35 g, 4.94 mmol) was added in small portions. After stirring at −5° C. for 1 h 2N sodium hydroxide solution (15 mL) was added dropwise. After 10 min additional 2N sodium hydroxide solution (60 mL) was added. The aqueous layer was extracted with ethyl acetate (3×40 mL). The combined organic layers were washed with water (30 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography (silica, dichloromethane, methanol). Yield: 0.16 g (7%).

Workup

  1. additionwas added dropwise
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×40 mL)
  3. washThe combined organic layers were washed with water (30 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography (silica, dichloromethane, methanol)

Sources & evidence

ORD record
ord-72f76fe697c84f53b3accfbb8903351c
Source dataset
uspto-grants-2014_02
Patent number
US08642587B2

Reaction notes

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