Cyclopropylboronic acid → HCID 44578967, compound

HRID 1443066Notes

Reaction equation

Br[C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[O:4][CH:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:6]1[CH2:11][NH:10][C:9](=O)[CH2:8][O:7]1.[CH:23]1(B(O)O)[CH2:25][CH2:24]1>>[CH:23]1([C:2]2[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=2[O:4][C@@H:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:6]2[O:7][CH2:8][CH2:9][NH:10][CH2:11]2)[CH2:25][CH2:24]1

Participants

Reactant 2

HCID 2760897Cyclopropylboronic acid

HCID 68539147HCID 68539147, compound

Product 1

HCID 44578967HCID 44578967, compound

Procedure

(S)-2-[(S)-(2-Cyclopropyl-phenoxy)-phenyl-methyl]-morpholine was synthesized from 6-[(2-Bromo-phenoxy)-phenyl-methyl]-morpholin-3-one and cyclopropyl boronic acid according to general procedures A and B and was isolated as a viscous colorless oil. 1H NMR (CDCl3): δ 7.40-7.24 (m, 5H), 6.91 (m, 1H), 6.80 (m, 2H), 6.66 (d, 1H), 5.15 (d, 1H), 3.94 (m, 2H), 3.65 (dt, 1H), 2.85-2.59 (m, 4H), 2.32 (m, 1H), 0.99-0.89 (m, 2H), 0.74-0.59 (m, 2H); MS (ES) 310.1 [C20H23NO2+H]+; HPLC purity (98.6%); Analysis: Calc'd for C20H23NO2: C, 77.64; H, 7.49; N, 4.53. Found: C, 76.61; H, 7.58; N, 4.37.

Workup

customwas isolated as a viscous colorless oil

Sources & evidence

ORD record: ord-1ddf9c32f4ef465faa150da1d27f65ce
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659394B2

Reaction notes

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