Trifluoroacetic acid → ethyl 3-(((2R,4R)-4-(benzyloxymethoxy)pyrrolidin-2-yl)methoxy)picolinate

HRID 869659Notes

Reaction equation

[CH2:1]([O:8][CH2:9][O:10][C@H:11]1[CH2:15][N:14](C(OC(C)(C)C)=O)[C@@H:13]([CH2:23][O:24][C:25]2[C:26]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[N:27][CH:28]=[CH:29][CH:30]=2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:8][CH2:9][O:10][C@H:11]1[CH2:15][NH:14][C@@H:13]([CH2:23][O:24][C:25]2[C:26]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[N:27][CH:28]=[CH:29][CH:30]=2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To an ice-cold solution of ethyl 3-(((2R,4R)-4-(benzyloxymethoxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)methoxy)picolinate (845 mg, 1.74 mmol, EXAMPLE 79 Step 3) in dichloromethane (12 mL) was added trifluoroacetic acid, and the mixture was stirred at 0° C. for 1 h. The mixture was warmed to room temperature and stirred for 1 h at this temperature, then the mixture was concentrated in vacuo to afford an oil. The residual oil was purified by NH-gel column chromatography (ethyl acetate only to methanol/ethyl acetate 1:10) to give 200 mg (30%) of the title compound as a pale yellow oil.

Workup

temperatureThe mixture was warmed to room temperature
stirringstirred for 1 h at this temperature
concentrationthe mixture was concentrated in vacuo
customto afford an oil
customThe residual oil was purified by NH-gel column chromatography (ethyl acetate only to methanol/ethyl acetate 1:10)

Sources & evidence

ORD record: ord-02c9b88c56aa4a7d88ef201a6bad974f
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969383B2

Reaction notes

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