Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → tert-Butyl (2S)-(adamant-1-ylmethoxycarbonylamino)-3-tert-butoxycarbonylaminopropionate

関与物質

役割	名称	HCID	仕込み量
反応物	Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol	HCID 64556	—
反応物	1,1'-Carbonyldiimidazole	HCID 68263	—
反応物	Diisopropylethylamine	HCID 81531	—
反応物	(S)-tert-Butyl 2-amino-3-((tert-butoxycarbonyl)amino)propanoate hydrochloride	HCID 86585733	—
溶媒	Tetrahydrofuran	HCID 8028	—
生成物	tert-Butyl (2S)-(adamant-1-ylmethoxycarbonylamino)-3-tert-butoxycarbonylaminopropionate	HCID 68828668	—

反応条件

温度	60 °C

反応手順

A solution of 10.9 g (65.4 mmol) of (1-hydroxymethyl)adamantane and 10.6 g (65.4 mmol) of carbonyldiimidazole in 60 ml of THF is stirred at 50° C. for 1.5 h. 9.7 g (32.7 mmol) of (13.9) in 25 ml of THF and 5.6 ml (32.7 mmol) of diisopropylethylamine (DIPEA) are added and the mixture is stirred at 60° C. for 4 h and then left to stand at room temperature overnight. The solvent is removed in vacuo and the residue is chromatographed through silica gel using heptane/ethyl acetate=7/3. 8.7 9 (59%) of (13.10) are obtained as a colorless oil.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US06218415B1
出典データセット	uspto-grants-2001_04
ORD ID	ord-792933421eae4e7fbca11c9b232f95ea
出典メモ	uspto-grants-2001_04