Acetyl chloride → 4-Aminotricyclo[3.3.1.1~3,7~]decane-1-carboxylic acid--hydrogen chloride (1/1)

HRID 1519070Notes

Reaction equation

C([Cl:4])(C)=O.[NH2:5][CH:6]1[CH:13]2[CH2:14][C:9]3([C:16]([OH:18])=[O:17])[CH2:10][CH:11]([CH2:15][CH:7]1[CH2:8]3)[CH2:12]2>CO>[ClH:4].[NH2:5][CH:6]1[CH:13]2[CH2:14][C:9]3([C:16]([OH:18])=[O:17])[CH2:10][CH:11]([CH2:15][CH:7]1[CH2:8]3)[CH2:12]2

Participants

Conditions

Temperature: 45 °C

Procedure

At 0° C., in a 250-mL flask, MeOH (85 ml) was added with AcCl (16.08 g, 204.85 mmol), and then at room temperature, 4-amino-adamantane-1-carboxylic acid (8.0 g, 40.97 mmol) was added thereto. At 45° C., the mixture was stirred for 12 hours. After the reaction was completed, the solid was filtered by acetonitrile to obtain 4-amino-adamantane-1-carboxylate hydrochloride (8.17 g, 81%).

Workup

filtrationthe solid was filtered by acetonitrile

Sources & evidence

ORD record: ord-bfe53dec20c841b79a2b92edfbbaa345
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073830B2

Reaction notes

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