ChemicalBook CAS DataBase List (1S-cis)-4-Amino-2-cyclopentene-1-methanol

(1S-cis)-4-Amino-2-cyclopentene-1-methanol synthesis

12synthesis methods

Product Name:(1S-cis)-4-Amino-2-cyclopentene-1-methanol
CAS Number:136522-35-5
Molecular formula:C6H11NO
Molecular Weight:113.16

229177-39-3
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(1S-cis)-4-Amino-2-cyclopentene-1-methanol

136522-35-5
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Yield: 49%

Reaction Conditions:

with hexahydro-2H-oxepin-2-one in tert-butyl methyl ether

Steps:

3 3.1.1 Preparation of (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene using lipases
3.1.1.4 11 mg of racemic cis-1-amino-4-(hydroxymethyl)-2-cyclopentene were stirred with 1 ml of methyl tert-butyl ether. 0.02 ml of 6-caprolactone and 20 U of Novozym 435 (immob. lipase from Candida antarctica) at room temperature. After 4 days, (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene with 87% ee was obtained in 49% yield (HPLC).

References:

Lonza AG US2002/10360, 2002, A1