2-Methoxyethylamine → HCID 58691194, compound

HRID 1392092Notes

Reaction equation

C(=O)(OC)O[CH2:3]/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:15][O:16][CH2:17][CH2:18][NH2:19]>CCO.CCOCC>[CH3:15][O:16][CH2:17][CH2:18][NH:19][C@H:5]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH:4]=[CH2:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (E)-cinnamyl methyl carbonate (0.50 g) in EtOH (10 mL) at RT under N2 was added the (S)-(1,1′-Dinaphthyl-2,2′-di-(S,S)-1-phenylethylphosphoramidite (0.140 g), [Ir(COD)Cl]2 (0.035 g) and 2-methoxyethylamine (0.39 g). The reaction mixture was stirred at 50° C. for 1.5 h, then cooled to RT. The reaction mixture was diluted with ether and washed with 2N HCl (×3). The combined acidic aqueous layer was made basic with aqueous 2N NaOH and extracted with DCM (×3). The combined DCM layer was washed with brine, dried (Na2SO4), filtered and evaporated The crude material was purified via column chromatography (gradient—5%, 10%, 15% EtOAc/hexanes) to give the desired product (0.375 g, 74% ee, 75% yield). 1H NMR (300 MHz, CDCl3) δ 2.62-2.81 (m, 2H), 3.34 (s, 3H), 3.49 (t, 2H), 4.18 (d, 1H), 5.09 (d, 1H), 5.20 (dd, 1H), 5.88-5.99 (m, 1H), 7.22-7.35 (m, 5H). MS APCI, m/z=192 (M+1). LC/MS 0.66 min., Method A.

Workup

temperaturecooled to RT
washwashed with 2N HCl (×3)
extractionextracted with DCM (×3)
washThe combined DCM layer was washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated The crude material
customwas purified via column chromatography (gradient—5%, 10%, 15% EtOAc/hexanes)

Sources & evidence

ORD record: ord-939fe94ec1894d13976f11e4b3daf6ff
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342007B2

Reaction notes

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