Cyanomethylenetributylphosphorane → 1-Boc-3-[5-bromo-2-(3-chloro-benzyloxy)-phenoxymethyl]-azetidin-3-ol

HRID 237304Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([OH:13])([CH3:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:14][C:15]1[CH:16]=[CH:17][C:18]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)=[C:19]([OH:21])[CH:20]=1.C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[C:6]([N:8]1[CH2:11][C:10]([CH2:12][O:21][C:19]2[CH:20]=[C:15]([Br:14])[CH:16]=[CH:17][C:18]=2[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)([OH:13])[CH2:9]1)([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

Conditions

Temperature: 150 °C

Procedure

The mixture of the title compound of Example 215 Step B (2.3 mmol), 5-bromo-2-(3-chloro-benzyloxy)-phenol (1.3 mmol), and cyanomethylenetri-n-butylphosphorane (2 mmol) in toluene (5 mL) was heated at 150° C. in a microwave reactor for 1 h. The mixture was cooled to rt and purified by PTLC providing the title compound (580 mg). MS (ESI): mass calcd. for C22H25BrClNO5, 497.1; m/z found, 504.2 [M-OH+Na]+. 1H NMR (CDCl3): 7.52-7.23 (m, 4H), 6.99-6.68 (m, 3H), 5.70-5.10 (br S, 1H), 5.04 (s, 2H), 4.99-4.97 (m, 2H), 4.50-4.46 (m, 4H), 1.45 (s, 9H).

Workup

temperatureThe mixture was cooled to rt
custompurified by PTLC

Sources & evidence

ORD record: ord-c15f8eeee3684f6caa903d2727301a9e
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642583B2

Reaction notes

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