Ethanol heptane → HCID 66732293, compound

HRID 1963618Notes

Reaction equation

HRID 1963618 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([F:25])[CH:24]=1)[CH2:5][C@H:6]1[CH2:11][C@@H:10]([C:12]2[O:16][NH:15][C:14](=[O:17])[CH:13]=2)[CH2:9][CH2:8][N:7]1[C:18]([O:20][CH3:21])=[O:19].CCCCCCC.CCO>CO>[F:25][C:23]1[CH:22]=[C:4]([CH:3]=[C:2]([F:1])[CH:24]=1)[CH2:5][C@H:6]1[CH2:11][C@@H:10]([C:12]2[O:16][NH:15][C:14](=[O:17])[CH:13]=2)[CH2:9][CH2:8][N:7]1[C:18]([O:20][CH3:21])=[O:19].[F:25][C:23]1[CH:22]=[C:4]([CH:3]=[C:2]([F:1])[CH:24]=1)[CH2:5][C@@H:6]1[CH2:11][C@H:10]([C:12]2[O:16][NH:15][C:14](=[O:17])[CH:13]=2)[CH2:9][CH2:8][N:7]1[C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 2

HCID 22502148Ethanol heptaneHCID 68500326HCID 68500326, compound

Product 2

HCID 66732293HCID 66732293, compoundYield 49%HCID 68500326HCID 68500326, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Cis-methyl 2-(3,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (1.604 g, 4.56 mmol) was subjected to chiral preparative HPLC (Column: Chiralpak AD (250×20), 5 μm particle size, mobile phase: Heptane/EtOH 90/10, flow rate 18 mL/min) to yield (2R,4S)-methyl 2-(3,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (645 mg, 40%), Chiral purity 99.2% ee, Optical rotation [α]D20=+13.1 (MeOH, c=1) and (2S,4R)-methyl 2-(3,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (789 mg, 49%), Chiral purity 99.6% ee, Optical rotation [α]D20=−10.1 (MeOH, c=1)

Sources & evidence

ORD record
ord-f0afb775495c4e3e92eef4b2a0fdeddb
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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