Methanesulfonyl chloride → (S)-tert-butyl 2-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)aziridine-1-carboxylate

HRID 1697258Notes

Reaction equation

HRID 1697258 reaction equation
[Si:1]([O:8][C@H:9]([CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[C@@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:11]O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].S(Cl)(C)(=O)=O.CC([O-])(C)C.[K+]>C(Cl)Cl>[Si:1]([O:8][C@@H:9]([CH:10]1[CH2:11][N@@:13]1[C:14]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:20])[CH2:21][O:22][Si:23]([C:26]([CH3:27])([CH3:29])[CH3:28])([CH3:25])[CH3:24])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 86635712tert-butyl (2S,3S)-3,4-bis(tert-butyldimethylsilyloxy)-1-hydroxybutan-2-ylcarbamate

Product 1

HCID 86635713(S)-tert-butyl 2-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)aziridine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl (2S,3S)-3,4-bis(tert-butyldimethylsilyloxy)-1-hydroxybutan-2-ylcarbamate (1.025 g, 2.3 mmol) in 20 mL DCM was cooled to 0° C., treated with N,N-DIPEA (0.60 ml, 3.4 mmol) followed by Ms-Cl (0.18 ml, 2.3 mmol). After stirring at 0° C. for 2 hours, the reaction mixture was concentrated in vacuo and the crude residue was dissolved in 20 mL THF. KOt-Bu (0.51 g, 4.6 mmol) was added, and the reaction mixture was allowed to stir at RT for 10 minutes. The reaction mixture was then diluted with EtAOc, washed with water then brine. The organics dried over MgSO4 and concentrated in vacuo. Purification of the crude residue by column chromatography gave (S)-tert-butyl 2-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)aziridine-1-carboxylate as a clear oil.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionthe crude residue was dissolved in 20 mL THF
  3. stirringto stir at RT for 10 minutes
  4. additionThe reaction mixture was then diluted with EtAOc
  5. washwashed with water
  6. dry with materialThe organics dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude residue by column chromatography

Sources & evidence

ORD record
ord-4bd087b12c744616b39de9cada4ebf60
Source dataset
uspto-grants-2012_04
Patent number
US08163909B2

Reaction notes

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