Triphenylphosphine → HCID 68578192, compound

HRID 1505626Notes

Reaction equation

HRID 1505626 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:17][CH2:18]O)[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([OH:20])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[CH2:8][N:9]([C:10]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:16])[CH2:17][CH2:18][O:20][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 86690657HCID 86690657, compound

Product 1

HCID 68578192HCID 68578192, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-[(4-bromo-2-hydroxy-phenyl)methyl]-N-(2-hydroxyethyl)carbamate (3 g, 8.67 mmol) and triphenylphosphine (3.4 g, 13.0 mmol) in dichloromethane (85 mL) was added diisopropyl azodicarboxylate (2.69 g, 13.0 mmol) and the reaction was stirred at ambient temperature for 12 hours. The reaction was then washed with water, brine, dried with MgSO4 and purified by silica gel column chromatography (0-40% EtOAc in heptane) to give tert-butyl 8-bromo-2,3-dihydrobenzo[f][1,4]oxazepine-4(5H)-carboxylate (2.45 g, 86% yield). LCMS (m/z) ES+ 328 [M+1]+.

Workup

  1. washThe reaction was then washed with water, brine
  2. dry with materialdried with MgSO4
  3. custompurified by silica gel column chromatography (0-40% EtOAc in heptane)

Sources & evidence

ORD record
ord-bdc5614897f54a279bc40180c4fd5fd2
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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