4-Toluenesulfonyl chloride → Tert-butyl 2-methylaziridine-1-carboxylate

HRID 556707Notes

Reaction equation

HRID 556707 reaction equation
O[CH2:2][C@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].CC1C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[K+]>C(OCC)C>[CH3:2][CH:3]1[CH2:4][N@:5]1[C:6]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:12]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 13200309tert-butyl N-((2R)-1-hydroxypropan-2-yl)carbamate

Product 1

HCID 10942718Tert-butyl 2-methylaziridine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (R)-tert-butyl 1-hydroxypropan-2-ylcarbamate (756 mg, 4.31 mmol) and 4-methylbenzene-1-sulfonyl chloride (905 mg, 4.75 mmol) in ethyl ether (30 mL) was added powdered potassium hydroxide (968 mg, 17.26 mmol) and reaction was refluxed for 2 hr. The reaction mixture was poured into a separatory funnel that contained crushed ice and extracted with ether (2×20 mL). The organics were combined, dried with sodium sulfate, filtered, and concentrated. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.16 (d, J=5.43 Hz, 3H) 1.38 (s, 9H) 1.83 (d, J=3.73 Hz, 1H) 2.17 (d, J=5.76 Hz, 1H) 2.40 (qd, J=5.65, 3.73 Hz, 1H).

Workup

  1. temperaturewas refluxed for 2 hr
  2. additionThe reaction mixture was poured into a separatory funnel that
  3. customcontained crushed ice
  4. extractionextracted with ether (2×20 mL)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-38f813628bda4be5b1c60d38f695631c
Source dataset
uspto-grants-2011_11
Patent number
US08058293B2

Reaction notes

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