Triphenylphosphine → N-tert-butyl-3-hydroxymethyl-3-nitroazetidine hydrochloride

HRID 1742075Notes

Reaction equation

HRID 1742075 reaction equation
[ClH:1].[C:2]([NH:6][CH2:7][C:8]([CH2:14]O)([N+:11]([O-:13])=[O:12])[CH2:9][OH:10])([CH3:5])([CH3:4])[CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[ClH:1].[OH:10][CH2:9][C:8]1([N+:11]([O-:13])=[O:12])[CH2:7][N:6]([C:2]([CH3:5])([CH3:4])[CH3:3])[CH2:14]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 190101112-[(tert-Butylamino)methyl]-2-nitropropane-1,3-diol Hydrochloride

Product 1

HCID 19010110N-tert-butyl-3-hydroxymethyl-3-nitroazetidine hydrochlorideYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of example 2 was ring closed by dissolving 0.243 g (1 mmol) of the product in 10 ml of tetrahydrofuran (THF) and 0.262 g (1 mmol) of triphenylphosphine at room temperature. Diethylazodicarboxylate (0.174 g, 1 mmol) was slowly added dropwise. Color instantly appeared and a white solid precipitated. The solid was filtered from the solution and dried to yield a product (70% of theoretical yield) of 3-hydroxymethyl-3-nitro-1-tertiarybutylazetidine hydrochloride as determined by 1H-nmr.

Workup

  1. customclosed
  2. customa white solid precipitated
  3. filtrationThe solid was filtered from the solution
  4. customdried

Sources & evidence

ORD record
ord-911d8e223d9c4de3b5985c2be0fb560c
Source dataset
uspto-grants-1994_08
Patent number
US05336784

Reaction notes

Loading…