Triphenylphosphine → HCID 18518335, compound

HRID 1369261Notes

Reaction equation

HRID 1369261 reaction equation
C(OC([N:8]([C:10]1[N:15]=[C:14]([CH:16](O)[CH3:17])[CH:13]=[CH:12][CH:11]=1)[CH3:9])=O)(C)(C)C.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH:33][C:34]1[CH:35]=[CH:36][C:37]2[CH2:43][CH:42]([CH2:44][C:45]([O:47]CC)=[O:46])[C:41]3[CH:50]=[CH:51][CH:52]=[CH:53][C:40]=3[O:39][C:38]=2[CH:54]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH3:9][NH:8][C:10]1[N:15]=[C:14]([CH2:16][CH2:17][O:33][C:34]2[CH:35]=[CH:36][C:37]3[CH2:43][CH:42]([CH2:44][C:45]([OH:47])=[O:46])[C:41]4[CH:50]=[CH:51][CH:52]=[CH:53][C:40]=4[O:39][C:38]=3[CH:54]=2)[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 18340683HCID 18340683, compoundHCID 18518255HCID 18518255, compound

Product 1

HCID 18518335HCID 18518335, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6-[N-(tert-butoxycarbonyl)-N-methylamino]-2-pyridylethanol (397 mg, 1.58 mmole) and diisopropyl azodicarboxylate (0.31 mL, 1.58 mmole) in anhydrous CH2Cl2 (8 mL) was added dropwise over 10 min to a solution of ethyl (±)-10, 11-dihydro-3-hydroxydibenzo[b,f]oxepine-10-acetate (186 mg, 0.63 mmole) and triphenylphosphine (413 mg, 1.58 mmole) in anhydrous CH2Cl2 (3.2 mL) at RT under argon. After 22 hr, the reaction was concentrated on the rotavap, and the residue was flash chromatographed on silica gel (2-13% EtOAc/hexanes) to give the title compound (146 mg,44%) as a clear oil: MS (ES) m/e 533.0 (M+H)+.

Workup

  1. concentrationthe reaction was concentrated on the rotavap
  2. customchromatographed on silica gel (2-13% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9616a1be419d48fabf77ebf089e3b028
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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