Hydrochloric Acid → HCID 11531386, compound

HRID 1253837Notes

Reaction equation

HRID 1253837 reaction equation
[BH4-].[Li+].C([O:5][C:6]([CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]3[N:21]([C:25]4[C:30]([CH3:31])=[CH:29][C:28]([Cl:32])=[CH:27][C:26]=4[CH3:33])[CH:22]=[C:23]([CH3:24])[C:15]=23)[CH2:10][CH2:9]1)=O)C.Cl.[OH-].[Na+]>O1CCCC1.O.CO>[Cl:32][C:28]1[CH:29]=[C:30]([CH3:31])[C:25]([N:21]2[C:16]3=[N:17][C:18]([CH3:20])=[CH:19][C:14]([N:11]4[CH2:10][CH2:9][CH:8]([CH2:6][OH:5])[CH2:13][CH2:12]4)=[C:15]3[C:23]([CH3:24])=[CH:22]2)=[C:26]([CH3:33])[CH:27]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 59845591HCID 59845591, compound

Product 1

HCID 11531386HCID 11531386, compoundYield 60.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium borohydride (4.11 g) in tetrahydrofuran (50 mL) was added a solution of 1-[1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidine-4-carboxylic acid ethyl ester (16.6 g) in a mixture of tertrahydrofuran (80 mL) and methanol (7.7 mL) in an ice-cooling bath. The mixture was stirred at room temperature for 2 hours. After cooling with an ice-cooling bath, water was added and the mixture was poured slowly into a 3M HCl aqueous solution. The solution was made to alkaline (pH=8) with 4 M NaOH aqueous solution to give a solid. The solid was collected by filtration and washed with water and diethylether. The solid was recrystallized from a mixture of ethanol and ethyl acetate to give {1-[1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl}methanol (9.1 g).

Workup

  1. temperaturecooling bath
  2. temperaturecooling bath
  3. customto give a solid
  4. filtrationThe solid was collected by filtration
  5. washwashed with water and diethylether
  6. customThe solid was recrystallized from a mixture of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-095058be393b48778d028ca521317eeb
Source dataset
uspto-grants-2013_06
Patent number
US08455511B2

Reaction notes

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