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

反応物 3

HCID 6367Acetyl chloride

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

生成物 1

HCID 14988810N-[(1S,2S)-2-Hydroxycyclopentyl]acetamide

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-efd939ad30ac4a92ac33415c127fd8d3
出典データセット: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US05043341

反応ノート

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