Dichloromethane → (trans)-Naphthalen-2-ylmethyl 3-fluoro-4-(tosyloxy)pyrrolidine-1-carboxylate

HRID 1095749Notes

Reaction equation

[F:1][C@H:2]1[C@H:6]([OH:7])[CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)=[O:9])[CH2:3]1.C(Cl)Cl.[CH3:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>CN(C1C=CN=CC=1)C.O>[F:1][C@H:2]1[C@H:6]([O:7][S:32]([C:29]2[CH:30]=[CH:31][C:26]([CH3:25])=[CH:27][CH:28]=2)(=[O:34])=[O:33])[CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)=[O:9])[CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

A flask was charged with (trans)-naphthalen-2-ylmethyl 3-fluoro-4-hydroxypyrrolidine-1-carboxylate (237 mg, 0.819 mmol), TEA (0.343 ml, 2.458mmol) and DMAP (10.0 mg, 0.082 mmol) in DCM (4.3 ml, 0.86 mmol). The reaction mixture was cooled to 0° C., and 4-methylbenzene-1-sulfonyl chloride (234 mg, 1.23 mmol) was added. The reaction was warmed to ambient temperature and stirred for 3 hours. The reaction was diluted with water and extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography, eluting with 0-5% MeOH in DCM to give the product as an oil (160 mg, 44% yield).

Workup

temperatureThe reaction was warmed to ambient temperature
extractionextracted with DCM
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated
customThe residue was purified by flash column chromatography
washeluting with 0-5% MeOH in DCM

Sources & evidence

ORD record: ord-c07f3daf9746479ea854106d1e3f9d9f
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138181B2

Reaction notes

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