Carbon Dioxide → HCID 178483631, compound

HRID 967172Notes

Reaction equation

C(=O)=O.C([O:6][C:7](=O)/[CH:8]=[CH:9]/[C@H:10]1[CH2:15][CH2:14][C@H:13]([CH2:16][CH2:17][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH3:19])[CH2:12][CH2:11]1)C.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1.CO>[C:23]([O:22][C:20](=[O:21])[N:18]([CH2:17][CH2:16][C@H:13]1[CH2:12][CH2:11][C@H:10](/[CH:9]=[CH:8]/[CH2:7][OH:6])[CH2:15][CH2:14]1)[CH3:19])([CH3:24])([CH3:26])[CH3:25]

Participants

Conditions

Temperature: -75 °C

Procedure

To a dry ice-cooled solution of 4 g (11.8 mmol) trans-3-{4-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-cyclohexyl}-(E)-acrylic acid ethyl ester (example 11.10) in 50 ml of tetrahydrofuran was added at −75° C. to −63° C. within 15 minutes 23.6 ml (28.3 mmol) of a solution of diisobutyl-aluminium hydride (1.2M in toluene). After the reaction mixture was stirred for 2 hours at −75° C., 20 ml of methanol was added at −75° C. to this mixture. The temperature was raised to 20° C. and 20 ml 1N hydrogen chloride solution was added. The reaction mixture was partitioned between ether, 1N hydrogen chloride solution, sodium hydrogen carbonate solution and water. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure giving 3.61 g of trans-{2-[4-(3-hydroxy-(E)-propenyl)-cyclohexyl]-ethyl}-methyl-carbamic acid tert-butyl ester as slightly yellow viscous oil, MS: 298 (MH+).

Workup

temperatureThe temperature was raised to 20° C.
customThe reaction mixture was partitioned between ether, 1N hydrogen chloride solution, sodium hydrogen carbonate solution and water
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-20ad2af8906241ca8be195d9bfd975d1
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06953806B2

Reaction notes

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