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

HRID 1416631Notes

Reaction equation

HRID 1416631 reaction equation
CC1C=C(Br)C=CC=1S(NC1C=C2N(C)C(N(C)C2=CC=1OC)=O)(=O)=O.[C:27]([N:34]1[CH2:37][CH2:36][C@H:35]1[CH2:38][OH:39])([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].[Br:40][C:41]1[CH:42]=[C:43](O)[CH:44]=[N:45][CH:46]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:27]([N:34]1[CH2:37][CH2:36][C@H:35]1[CH2:38][O:39][C:43]1[CH:44]=[N:45][CH:46]=[C:41]([Br:40])[CH:42]=1)([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5995293-Bromo-5-hydroxypyridineHCID 5462977Diethyl azodicarboxylateHCID 131721282HCID 131721282, compound

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-0bfe5cf078a0491985622422bc7bfd87
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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