Hexane → tert-butyl {[(1S,2S)-2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}carbamate

HRID 1639855Notes

Reaction equation

HRID 1639855 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][C@@H:9]1[CH2:11][C@H:10]1[C:12]1[C:13]2[C:17]([CH:18]=[CH:19][CH:20]=1)=[N:16][N:15]([CH3:21])[CH:14]=2)([CH3:4])([CH3:3])[CH3:2].CC(NCCC#N)CC1C=CC=CC=1.Cl.CCCCCC>C(O)C>[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][C@H:9]1[CH2:11][C@@H:10]1[C:12]1[C:13]2[C:17]([CH:18]=[CH:19][CH:20]=1)=[N:16][N:15]([CH3:21])[CH:14]=2)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 8058HexaneHCID 161245Fenproporex hydrochlorideHCID 59334523tert-butyl {[(1R,2R)-2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}carbamate

Product 1

HCID 59334516tert-butyl {[(1S,2S)-2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}carbamateYield 49.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Trans-tert-butyl{[2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}carbamate (5.90 g) was fractionated by high performance liquid chromatography (instrument: Prep LC 2000 (manufactured by Nihon Waters K.K.), column: CHIRALPAK AD (50 mm ID×500 mm L, manufactured by Dicel Chemical Industries, Ltd.), mobile phase: A) hexane 100%, B) ethanol 100%, mixing ratio: A/B=900/100, flow rate: 80 mL/min, column temperature: 30° C., sample injection amount: 200 mg (dissolved in 100 mL of mobile phase). A fraction solution containing an optically active compound having a shorter retention time under the above-mentioned high performance liquid chromatography conditions was concentrated to give the title compound (2.92 g, 99.6% ee). Enantiomer excess (ee) was measured by high performance liquid chromatography (column: CHIRALPAK AD (4.6 mm ID×250 mm L, manufactured by Dicel Chemical Industries, Ltd.), mobile phase: hexane/ethanol=900/100, flow rate: 1.0 mL/min, column temperature: 30° C., sample concentration: 0.5 mg/mL (mobile phase), injection volume: 10 μL).

Workup

  1. additionA fraction solution containing an optically active compound
  2. concentrationwas concentrated

Sources & evidence

ORD record
ord-a32c023392bf40eab093a52f78b716e7
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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