Triphenylphosphine → (S)-Tert-butyl 2-(((5-bromopyridin-3-YL)oxy)methyl)azetidine-1-carboxylate

HRID 617337Notes

Reaction equation

HRID 617337 reaction equation
[C:1]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][OH:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:14][C:15]1[CH:16]=[C:17](O)[CH:18]=[N:19][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:17]1[CH:18]=[N:19][CH:20]=[C:15]([Br:14])[CH:16]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5995293-Bromo-5-hydroxypyridineHCID 5462977Diethyl azodicarboxylateHCID 10511797tert-butyl (2S)-2-(hydroxymethyl)azetidine-1-carboxylate

Product 1

HCID 10688713(S)-Tert-butyl 2-(((5-bromopyridin-3-YL)oxy)methyl)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 619.3 mg (3.31 mmol) sample of 1-BOC-2-(S)-azetidinemethanol, prepared as in Example 7b above, and 480 mg (2.76 mmol) of 5-bromo-3-hydroxypyridine, from Example 65b above, were reacted with triphenylphosphine and DEAD (3.31 mmol each) in 10 mL of THF according to the procedure of Example 14a, to give 887 mg of the title compound. MS (DCI/NH3) m/e 243/246 (M+H)+, 260/262 (M+NH4)+. 1H NMR (CDCl3, 300 MHz) δ: 8.35-8.25 (br, 2H), 7.44 (s, 1H), 4.55-4.47 (m, 1H), 4.39-4.29 (m, 1H), 4.16-4.10 (m, 1H), 3.98-3.85 (m, 2H), 2.42-2.33 (m, 2H), 1.42 (s, 9H).

Sources & evidence

ORD record
ord-e4d4c41519284c9b9732935b28677688
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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