Reaction:JCGG-RAC0000851

JCGG ID		JCGG-RAC0000851
Submitter		The Noguchi Institute
Reaction ID		R-0000-000851
Regist Date		2012/06/21 16:26:29
REACTANT
MOLECULE ID		JCGG-COM0000974 (Reaction Tree)
	Reactant Type	N-Cbz-4-hydroxy-D-proline methyl ester
	Mol	4.4 mmol
MOLECULE ID		JCGG-COM0000047
	Reactant Type	Et3N
	Mol	4.87 mmol
MOLECULE ID		JCGG-COM0000975
	Reactant Type	MsCl
	Mol	5.76 mmol
MOLECULE ID		JCGG-COM0000500
	Reactant Type	DMAP
	Mol	catalytic amount
MOLECULE ID		JCGG-COM0000776
	Reactant Type	NaBH4
	Mol	0.7 mmol
MOLECULE ID		JCGG-COM0000976
	Reactant Type	PhSe-SePh
	Mol	0.35 mmol
PRODUCT
MOLECULE ID		JCGG-COM0000977 (Reaction Tree)
	Product Type	(phenylselenyl)proline derivative
	Yield	63%
REACTION DETAIL
Reaction Time		1.5 hours, 2 hours
Reaction Temp		room temp, reflux
Solvent		CH2Cl2, EtOH
Catalyst		DMAP
Comment		1) N-Cbz-4-hydroxy-D-proline methyl ester+Et3N, MsCl, DMAP, 2) +NaBH4, PhSe-SePh
		The reactants were mixed at 0 degree in Celsius, and gradually raised to room temperature within the reaction time. (first phase)
		NaBH4 and PhSe-SePh were mixed independently and stirred for 5 minutes before poured into the solution from the first phase.
COMMENT
The PMID could not be found.
There are two phases in this reaction.
REFERENCE
Reference Id		REF-0000-000038
	Source	J. Am. Chem. Soc. 1996, 118, 6826-6840
	Doi	10.1021/ja952265x