Triphenylphosphine → tert-Butyl {2-[(pyridin-2-yl)oxy]ethyl}carbamate

HRID 500167Notes

Reaction equation

HRID 500167 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.O[CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[O:13][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 178516071HCID 178516071, compound

Product 1

HCID 68804906tert-Butyl {2-[(pyridin-2-yl)oxy]ethyl}carbamateYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (630 μL, 4.00 mmol) was added to a mixture of 2-hydroxypyridine (0.380 g, 4.0 mmol), tert-butyl (2-hydroxyethyl)carbamate (0.322 g, 2.0 mmol) and triphenylphosphine (1.05 g, 4.0 mmol) in THF (6.0 mL). The mixture was stirred overnight at RT, and concentrated. The residue was chromatographed on silica gel with EtOAc in hexanes to give the product (0.353 g, 74.1%). LCMS: (M+H)=239.2.

Workup

  1. concentrationconcentrated
  2. customThe residue was chromatographed on silica gel with EtOAc in hexanes

Sources & evidence

ORD record
ord-264000045a1c4fc6a1b0bf3e0df0b982
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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