Sodium cyanoborohydride → 4-Aminopyran-4-yl carboxylic acid t-butyl ester

HRID 8742Notes

Reaction equation

C(O[BH-](OC(=O)C)OC(=O)C)(=[O:3])C.[Na+].C([BH3-])#N.[Na+].[C:19]([O:23][C:24]([C:26]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>>[C:19]([O:23][C:24]([C:26]1([NH2:31])[CH:30]=[CH:29][O:3][CH:28]=[CH:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

Reactant 3

HCID 5003444Sodium cyanoborohydride

HCID 5049666Sodium triacetoxyborohydride

HCID 14161653Tert-butyl 1-aminocyclopentane-1-carboxylate

Product 1

HCID 695987624-Aminopyran-4-yl carboxylic acid t-butyl ester

Procedure

An alternative route for the preparation of some 1,3,4-trisubstituted cyclopentanes within the scope of the instant invention is given in Scheme 11. Reductive alkylation, using for example sodium triacetoxyborohydride or sodium cyanoborohydride, of a cycloalkyl amino-acid 11-2, such as 1-aminocyclopentane carboxylic acid t-butyl ester (Z=single bond) or a heterocyclic amino-acid, such as 4-aminopyran-4-yl carboxylic acid t-butyl ester (Z=O) with the ketone-alcohol 11-1 (Scheme 4) gives 11-3 and 11-4 as a mixture of C-1 isomers which may be separated. These intermediates can then be converted to the final product(s) 11-5 and/or 11-6 as described in Scheme 5.

Sources & evidence

ORD record: ord-5062c37bf9ad4880a95eebcce007759c
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091211B2

Reaction notes

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