(R)-2-Methyl-CBS-oxazaborolidine → HCID 44552953, compound

HRID 1037666Notes

Reaction equation

HRID 1037666 reaction equation
CO[N:3](C)[C:4]([C@H:6]1[CH2:11][CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7]1)=O.B1(C)O[C:26]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32]C=CC=2)[C@@H]2N1CCC2.[CH3:41][C:42]1[NH:46]N=[N:44][N:43]=1.N1C=NN=N1>>[CH3:41][C:42]1[N:43]=[N:44][N:3]([C@H:4]([C:33]2[CH:28]=[CH:26][C:34]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:32]=2)[C@H:6]2[CH2:11][CH2:10][CH2:9][NH:8][CH2:7]2)[N:46]=1

Participants

5

Reactant 4

HCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 30025967HCID 30025967, compoundHCID 178418441HCID 178418441, compoundHCID 178434708HCID 178434708, compound

Product 1

HCID 44552953HCID 44552953, compound

Procedure

The procedure given in Example 1 was followed using tert-butyl (3S)-3-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate was used instead of tert-butyl(3R)-3-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate. As a reducing agent, (R)-2-methyl-CBS-oxazaborolidine was used instead of (S)-2-methyl-CBS-oxazaborolidine. And 5-methyl-1H-tetrazole was used as a reactant, instead of 1H-tetrazole, to give (3S)-3-[(S)-(5-methyl-2H-tetrazol-2-yl)(naphthalen-2-yl)methyl]piperidine.

Sources & evidence

ORD record
ord-fb439589081e4e289ea5aff0fb2a3332
Source dataset
uspto-grants-2013_10
Patent number
US08546576B2

Reaction notes

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