Sulfuric Acid → (2S,5R)-benzyl 5-(benzyloxyamino)piperidine-2-carboxylate

HRID 508458Notes

Reaction equation

HRID 508458 reaction equation
[CH2:1]([O:8][C:9]([C@@H:11]1[CH2:16][CH2:15][C:14](=[N:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:13][NH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[BH4-].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]([C@@H:11]1[CH2:16][CH2:15][C@@H:14]([NH:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:13][NH:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 86702281Phenylmethyl (2S)-5-[(phenylmethoxy)imino]-2-piperidinecarboxylate

Product 1

HCID 70673934(2S,5R)-benzyl 5-(benzyloxyamino)piperidine-2-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

Under nitrogen atmosphere, tetrahydrofuran (2 ml) was added to (2S)-5-benzyloxyimino-piperidine-2-carboxylic acid benzyl ester (0.168 g, 0.50 mmol), and the mixture was cooled down to −10° C. Sulfuric acid (0.302 g, 3.06 mmol) was added to the mixture, and then sodium borohydride (0.0567 g, 1.50 mmol) was added. After 22 hours of stirring, the reaction mixture was analyzed with high performance liquid chromatography to find that the mixture contained 0.136 g of the title compound, and the reduction reaction proceeded with the yield of 80%. The diastereo selectivity was (2S,5R)/(2S,5S)=80.4/19.6 (60.8% de).

Sources & evidence

ORD record
ord-7c4c08d5f923470a9f47d97d0bae6bb5
Source dataset
uspto-grants-2015_08
Patent number
US09096523B2

Reaction notes

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