Ammonia → HCID 14817494、化合物

反応式

[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][CH:13]([OH:26])[CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][CH:19]([C:22]([O:24][CH3:25])=[O:23])[CH2:18][CH2:17]2)[CH2:7][CH2:6]1)([O:3][CH3:4])=[O:2].N>>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([CH2:15][CH2:14][CH:13]([OH:26])[CH2:12][CH2:11][C:8]2[CH:7]=[CH:6][C:5]([C:1]([O:3][CH3:4])=[O:2])=[CH:10][CH:9]=2)=[CH:21][CH:20]=1)([O:24][CH3:25])=[O:23]

参加物

反応物 2

HCID 222Ammonia

HCID 212560191,5-Bis-(4'-carbomethoxycyclohexyl)-3-pentanol

生成物 1

HCID 14817494HCID 14817494、化合物

実験手順

To a stainless steel autoclave was added 143.9 g (0.404 moles) 1,5-bis-(4'-carbomethoxyphenyl)-3-pentanol, 14.4 grams of 0.5% Pd on alumina, and 1,150 mL of cyclohexane. The autoclave was pressurized to 500 psi with hydrogen and then heated to 225° C. Upon reaching temperature, the pressure was adjusted to 1500 psi and these conditions were maintained for 6 hrs. The reaction was then cooled and vented. The product is soluble in the cyclohexane and is separated from the catalyst by filtration. The product is isolated by simple solvent removal in vacuo to give 139.6 grams of product (0.379 moles, 94%) consisting of all three diastereomeric cyclohexyl isomers of 1,5-bis -(4'-carbomethoxycyclohexyl)-3-pentanol. 300 MHz NMR (CDCl3) δ=0.93 (m,2H), 1.10-1.65 (m, 20H), 1.82 (d,1H), 1.96 (d,4H), 2.23 (m,1H), 2.52 (m,1H), 3.53 (s(br), 1H), 3.67 (s,3H), 3.69 (s,3H). IR (neat): 1040, 1200, 1740, 3500 cm-1. GC-MS: (a) electron impact 50 eV: all three isomers with identical mass spectra: 368(<1%), 350, 337, 318, 290, 199, 170, 167, 138, 121, 108, 95, 94, 87, 81, 67. (NH3 chemical ionization): three peaks with M+=368.

出典と根拠

ORDレコード: ord-c5d51dd0152a479f8a2feb48f0acaa22
出典データセット: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US05144003

反応ノート

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