Diethyl Ether → HCID 67120682, compound

HRID 1665100Notes

Reaction equation

NN.[C:3]([O:7][C:8](=[O:44])[NH:9][C@H:10]([CH2:32][N:33]1C(=O)C2C(=CC=CC=2)C1=O)[CH2:11][C:12]([CH3:31])([CH3:30])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@@H:23]2[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24]2)=[CH:17][CH:16]=1)([CH3:6])([CH3:5])[CH3:4].C(OCC)C>C1COCC1.C(O)C>[C:3]([O:7][C:8](=[O:44])[NH:9][C@H:10]([CH2:32][NH2:33])[CH2:11][C:12]([CH3:31])([CH3:30])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@@H:23]2[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24]2)=[CH:17][CH:16]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

Conditions

Temperature: 45 °C

Procedure

Hydrazine (2.2 ml of a 1M solution in THF, 2.2 mmol) is added to a solution of [(S)-5-[4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-1-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3,3-dimethyl-pentyl]-carbamic acid tert-butyl ester (0.16 g, 0.28 mmol) in ethanol (5 ml), and the resulting colourless solution is heated at 45° C. overnight. The reaction is allowed to cool to room temperature, and diethyl ether (30 ml) is added and the resulting white suspension cooled at 0° C. for 30 minutes. The white solid is removed by filtration, and the solvent removed in vacuo to yield {(S)-1-Aminomethyl-5-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-3,3-dimethyl-pentyl}-carbamic acid tert-butyl ester as a colourless oil; [M+H]+ 451.

Workup

temperatureto cool to room temperature
temperaturethe resulting white suspension cooled at 0° C. for 30 minutes
customThe white solid is removed by filtration
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-31027dcfa04c4df98df362104b6b0bc6
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039472B2

Reaction notes

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