Sodium hydride → 3-Butoxy-3-phenyl-1-(tert-butoxycarbonyl)azetidine

HRID 540368Notes

Reaction equation

[OH:1][C:2]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH2:3]([O:1][C:2]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1)[CH2:2][CH2:13][CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1 g (4.0 mmol) of 3-hydroxy-3-phenyl-1-(tert-butoxycarbonyl)azetidine dissolved in 5 ml of DMF is added dropwise to a suspension of 300 mg of 60% NaH in 3 ml of DMF, immersed in a bath at 0° C. 2.5 ml of n-iodobutane are added dropwise. The reaction medium is left to stir at 0° C. for 15 minutes and 72 hours at ambient temperature. The medium is hydrolysed by addition of a saturated solution of ammonium chloride, followed by extraction with ethyl acetate. The organic phase is dried and evaporated to dryness. The crude product obtained is purified on silica in a 7/3 heptane/ethyl acetate mixture. 500 mg in the form of a light yellow oil are obtained with a yield of 41%.

Workup

customimmersed in a bath at 0° C
waitThe reaction medium is left
extractionfollowed by extraction with ethyl acetate
customThe organic phase is dried
customevaporated to dryness

Sources & evidence

ORD record: ord-cf047b5578f342f7b5f324dc99f153bf
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871187B2

Reaction notes

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