Acetyl chloride → N-[(1S,2S)-2-Hydroxycyclopentyl]acetamide
Reaction equation
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]Participants
4
Procedure
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.
Sources & evidence
- ORD record
- ord-c0ef6b8729ea40178f4e24a8058c9301
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05141944
Reaction notes
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