3-Hydroxypyridine → 1-BOC-2-(R)-azetidinylmethoxy pyridine

HRID 1416627Notes

Reaction equation

HRID 1416627 reaction equation
[C:1](N1CC[C@@H]1CO)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.C1(P([C:34]2[CH:39]=[CH:38]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC[O:42][C:43](/[N:45]=N/C(OCC)=O)=O>C1COCC1>[C:1]([N:17]1[CH:18]=[CH:19][CH:20]=[CH:15][C@H:16]1[O:42][CH2:43][N:45]1[CH2:38][CH2:39][CH2:34]1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 4

HCID 79713-HydroxypyridineHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 11074142(R)-1-Boc-2-azetidinemethanol

Product 1

HCID 675853711-BOC-2-(R)-azetidinylmethoxy pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.10 g (5.87 mmol) sample of 1-BOC-2-(R)-azetidinemethanol, prepared in step 62b above, and 588 g (5.87 mmol) of 3-hydroxypyridine were reacted with triphenylphosphine and DEAD (7.05 mmol each) in 100 mL of THF according to the procedure of Example 14a, to give the title compound.

Sources & evidence

ORD record
ord-16551dd045a1450f80644941dd943e50
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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