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3 as a base was reported to give pyrrolidyl derivatives in moderate yields. Moffett, R. B. J. Org. Chem. 1949, 14, 2.
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15644367252
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This simple and efficient alkylation procedure has now been used to prepare a wide variety of N,N-cycloalkyl derivatives of amino alcohols
-
This simple and efficient alkylation procedure has now been used to prepare a wide variety of N,N-cycloalkyl derivatives of amino alcohols.
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25
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0000418334
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15644366742
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The reaction may alternately be quenched into 2 N aqueous HCl without loss of 2a into the aqueous phase. Aqueous HCl may also be used interchangeably with citric acid in purifying and recycling the ligand 5b
-
The reaction may alternately be quenched into 2 N aqueous HCl without loss of 2a into the aqueous phase. Aqueous HCl may also be used interchangeably with citric acid in purifying and recycling the ligand 5b.
-
-
-
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29
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15644365107
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The product 2a readily upgrades in optical purity upon crystallization
-
The product 2a readily upgrades in optical purity upon crystallization.
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-
30
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15644366289
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-
The less expensive quinone chloranil was also used for the deprotection step. However, the initial oxidation of 2a to give the cyclic aminals 13a/13b is not as efficient as the reaction involving DDQ, and aminals 13a/13b required purification (by crystallization) prior to conversion into the amino alcohol 2b. The isolated yield of 2b from this two-step procedure was 75-80%
-
The less expensive quinone chloranil was also used for the deprotection step. However, the initial oxidation of 2a to give the cyclic aminals 13a/13b is not as efficient as the reaction involving DDQ, and aminals 13a/13b required purification (by crystallization) prior to conversion into the amino alcohol 2b. The isolated yield of 2b from this two-step procedure was 75-80%.
-
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31
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0000096274
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The structure of 13b was determined by comprehensive heteronuclear NOE (HOESY) experiments. Yu, C.; Levy, G. C. J. Am. Chem. Soc. 1984, 106, 6533.
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15644374100
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3 ensures pH < 8.5 and complete formation of the carbamate 14b before addition of KOH to effect ring closure
-
3 ensures pH < 8.5 and complete formation of the carbamate 14b before addition of KOH to effect ring closure.
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