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

HRID 1257824Notes

Reaction equation

HRID 1257824 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.[C:20]([O:24][C:25](=[O:30])[NH:26][CH2:27][CH2:28]O)([CH3:23])([CH3:22])[CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:20]([O:24][C:25](=[O:30])[NH:26][CH2:27][CH2:28][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)([CH3:23])([CH3:22])[CH3:21]

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-73bdf0b777b1462e833e64d40dd19026
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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