(1R,2S,3R,4R)-2,3-DIHYDROXY-4-(HYDROXYMETHYL)-1-AMINOCYCLOPENTANE HYDROCHLORIDE synthesis
- Product Name:(1R,2S,3R,4R)-2,3-DIHYDROXY-4-(HYDROXYMETHYL)-1-AMINOCYCLOPENTANE HYDROCHLORIDE
- CAS Number:79200-57-0
- Molecular formula:C6H14ClNO3
- Molecular Weight:183.63
79200-54-7
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Yield:-
Reaction Conditions:
with lithium borohydride in tetrahydrofuran at 0 - 20;
Steps:
4.C Step C: (1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol hydrochloride (4-4)
To a mixture of 4-3 (2.1 g, 9.9 mmol) in THF (10 [ML)] was added lithium borohydride (0.32 g, 14.6 mmol) under cooling to ice temperature and the reaction mixture was stirred at room temperature overnight, evaporated in vacuo and treated with methanol. The mixture was cooled in an ice-bath and acidified with 0. 1N [HC1.] The solvent was removed in vacuo and triturated with acetone. The residual oil was dried in vacuo and used without further purification as shown in Scheme 6 in the synthesis of 6-6.
References:
Merk & Co., Inc.;ISIS Pharmaceuticals, Inc. WO2003/105770, 2003, A2 Location in patent:Page 46-47