Lithium Hydroxide → N-(3-amino-4-methylcyclopentyl)cyclopropanesulfonamide

HRID 1969656Notes

Reaction equation

HRID 1969656 reaction equation
[N:1]([CH:4]1[CH:8]([CH3:9])[CH2:7][CH:6]([NH:10][S:11]([CH:14]2[CH2:16][CH2:15]2)(=[O:13])=[O:12])[CH2:5]1)=C=O.[Li+].[OH-]>C1COCC1>[NH2:1][CH:4]1[CH:8]([CH3:9])[CH2:7][CH:6]([NH:10][S:11]([CH:14]2[CH2:15][CH2:16]2)(=[O:13])=[O:12])[CH2:5]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86660440N-(3-isocyanato-4-methylcyclopentyl)cyclopropanesulfonamide

Product 1

HCID 67216953N-(3-amino-4-methylcyclopentyl)cyclopropanesulfonamideYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of N-(3-isocyanato-4-methylcyclopentyl)cyclopropanesulfonamide (1.00 g, 4.09 mmol, Preparation #NNN.1) in THF (2.0 mL) was added aqueous LiOH (4 N, 20.5 mL, 82 mmol). The reaction was heated to about 50° C. for about 16 h, cooled to ambient temperature and partitioned between water (5 mL) and EtOAc (10 mL). The organic portion was separated and the aqueous portion was extracted with DCM (3×20 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered, and concd under reduced pressure to give crude N-(3-amino-4-methylcyclopentyl)cyclopropanesulfonamide (0.66 g, 74%) as a white solid: LC/MS (Table 1, Method n) Rt=0.020 min; MS m/z: 219 (M+H)+.

Workup

  1. temperaturecooled to ambient temperature
  2. custompartitioned between water (5 mL) and EtOAc (10 mL)
  3. customThe organic portion was separated
  4. extractionthe aqueous portion was extracted with DCM (3×20 mL)
  5. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-7b78a8d480674f17b1f50911b96620de
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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