Hydrochloric Acid → HCID 22736527, compound

HRID 51064Notes

Reaction equation

HRID 51064 reaction equation
[CH3:1][CH:2]([CH3:17])[CH2:3][CH2:4][NH:5][C:6]([C:8]1([C:13](OC)=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]1)=O.Cl.[OH-].[Na+]>C1COCC1.O>[CH3:1][CH:2]([CH3:17])[CH2:3][CH2:4][NH:5][CH2:6][C:8]1([CH2:13][OH:14])[CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22135199HCID 22135199, compound

Product 1

HCID 22736527HCID 22736527, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of methyl 1-[N-(3-methylbutyl)-carbamoyl]-cyclopentanecarboxylate (900 mg, 3.7 mmol) in THF at rt was added BH3/THF complex ) 7.4 mL, 7.4 mmol) and stirred at 75° C. for 5 hours. To this reaction mixture was added 6N HCl (10 mL) and the mixture was further stirred for 30 min before the solution was neutralized by 1N NaOH. The solution was diluted with water and extracted with EtOAc. The combined extracts were dried over magnesium sulfate, and concentrated to a crude oil (700 mg, 95%). MS [M+H]+200.

Workup

  1. stirringthe mixture was further stirred for 30 min before the solution
  2. extractionextracted with EtOAc
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. concentrationconcentrated to a crude oil (700 mg, 95%)

Sources & evidence

ORD record
ord-a5c29a430b75420d8359c63d0415a4dd
Source dataset
uspto-grants-2004_03
Patent number
US06713476B2

Reaction notes

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