Chloroacetyl chloride → trans-N-benzyl-2-chloro-N-(4-hydroxytetrahydrofuran-3-yl)acetamide

HRID 81165Notes

Reaction equation

[CH2:1]([NH:8][C@@H:9]1[CH2:13][O:12][CH2:11][C@H:10]1[OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:22][CH2:23][C:24](Cl)=[O:25]>C(Cl)Cl>[CH2:1]([N:8]([C@H:9]1[C@H:10]([OH:14])[CH2:11][O:12][CH2:13]1)[C:24](=[O:25])[CH2:23][Cl:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -40 °C

Procedure

To a solution of trans-4-(benzylamino)tetrahydrofuran-3-ol (4.1 g, 21.2 mmol) in CH2Cl2 (40 mL) at −40° C. was added triethylamine (5.9 mL, 42.4 mmol) followed by dropwise addition of 2-chloroacetyl chloride (1.6 mL, 21.2 mmol). The reaction was stirred at −40° C. for 2 hours. The reaction was quenched with saturated aqueous NaHCO3 (40 mL) and extracted using CH2Cl2 (100 mL). The organic layer was separated, washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Purification of the residue on a silica gel column with 0 to 100% EtOAc/hexanes afforded trans-N-benzyl-2-chloro-N-(4-hydroxytetrahydrofuran-3-yl)acetamide. MS APCl calc'd for C13H16ClNO3 [M+H]+270. found 270.

Workup

customThe reaction was quenched with saturated aqueous NaHCO3 (40 mL)
extractionextracted
customThe organic layer was separated
washwashed with brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification of the residue on a silica gel column with 0 to 100% EtOAc/hexanes

Sources & evidence

ORD record: ord-dac70294209e4de28c9def7c66a2cf41
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846657B2

Reaction notes

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