Ethyl Acetate → HCID 89077462, compound

HRID 1752835Notes

Reaction equation

[Br:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8](Br)=[O:9].Cl.C(O[NH2:20])C1C=CC=CC=1.CCO[C:24](C)=[O:25]>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][NH:20][CH:24]=[O:25]

Participants

Reactant 3

HCID 8857Ethyl Acetate

HCID 102312Benzyloxyamine hydrochloride

HCID 89077495HCID 89077495, compound

Product 1

HCID 89077462HCID 89077462, compoundYield 72%

Procedure

Prepared in 72% yield (4.5 g, 14.5 mmol) from the reaction of 2-bromocyclohexanoyl bromide (4.53 g, 20.1 mmol) with O-benzylhydroxylamine, hydrochloride (3.21 g, 20.1 mmol) via general procedure A. Rf=0.47 (3:1; hexanes:EtOAc); mp=84.6-86.1° C.; 1H NMR (400 MHz, CDCl3) δ 8.98 (br s, 1H), 7.51-7.31 (m, 5H), 4.94 (s, 2H), 2.13 (ddd, J=14.6, 10.9, 4.0 Hz, 2H), 2.00 (dt, J=14.0, 4.1 Hz, 2H), 1.80-1.57 (m, 5H), 1.42-1.23 (m, 1H). 13C NMR (101 MHz, CDCl3) δ 169.6, 135.0, 129.6, 129.0, 128.7, 78.2, 38.1, 24.7, 22.6. IR (neat) 3235 (br), 3034, 2936, 2862, 1680, 1651 (s), 1470, 1459, 1270, 1249, 1210, 1122, 1025, 1000 cm-1; HR-APPIMS calculated for C14H16BrNO2 (M+H)+ 312.0594, observed 312.0206.

Sources & evidence

ORD record: ord-69e96f2266ca4ec381780585b2fe4c65
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163033B2

Reaction notes

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