Ethanol heptane → HCID 66739232, compound

HRID 1963504Notes

Reaction equation

HRID 1963504 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]2[CH2:12][CH:11]([C:13]3[O:17][NH:16][C:15](=[O:18])[CH:14]=3)[CH2:10][CH2:9][N:8]2[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])=[N:5][N:4]=[N:3]1.CCCCCCC.CCO>C(#N)C>[CH3:1][N:2]1[C:6]([C@H:7]2[CH2:12][C@@H:11]([C:13]3[O:17][NH:16][C:15](=[O:18])[CH:14]=3)[CH2:10][CH2:9][N:8]2[C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20])=[N:5][N:4]=[N:3]1

Participants

4

Reactant 2

HCID 22502148Ethanol heptaneHCID 66734753HCID 66734753, compound

Product 1

HCID 66739232HCID 66739232, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzyl 2-(1-methyl-1H-tetrazol-5-yl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (488 mg, 1.27 mmol) was subjected to chiral preparative HPLC (Column: Chiralpak AS (250×20), 5 μm particle size, mobile phase: Heptane/EtOH/DEA 60/40/0.1, flow rate 18 mL/min) to yield (2R,4S)-benzyl 2-(1-methyl-1H-tetrazol-5-yl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (231 mg, 47%), chiral purity 98% ee, Optical rotation [α]D20=+14.5 (acetonitrile, c=1)

Sources & evidence

ORD record
ord-2b74a1a8e7834b8896f5558a5ab9899a
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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