Acetyl chloride → N-[(1S,2S)-2-Hydroxycyclopentyl]acetamide
反応式
C(Cl)(=[O:3])C.[O:5]1C[CH2:8][CH2:7][CH2:6]1.C([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])C>>[OH:5][C@H:6]1[CH2:7][CH2:8][CH2:16][C@@H:15]1[NH:12][C:13](=[O:3])[CH3:14]参加物
4
実験手順
In addition, this intermediate can be acetylated with acetyl chloride in a solvent such as tetrahydrofuran in the presence of an acid scavenger, such as triethylamine, to give (S,S)-(+)-N-(2-hydroxycyclopentyl)acetamide. Treatment of this acetamide derivative with thionyl chloride results in the ring-closed intermediate (S,R)-4,5,6,6a-tetrahydro-2-methyl-3aH-cyclopentoxazole hydrochloride which is converted into (R,S)-(-)-2-aminocyclopentanol hydrochloride when allowed to reflux in the presence of dilute hydrochloric acid. This intermediate can then be used in any of the above schemes, preferably using the ergoline acid and carbonyldiimidazole, to give the (S,R) compound of this invention.
出典と根拠
- ORDレコード
- ord-c0ef6b8729ea40178f4e24a8058c9301
- 出典データセット
- uspto-grants-1992_08
- 特許番号
- US05141944
反応ノート
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