Hexane → HCID 67491040, compound

HRID 1917375Notes

Reaction equation

HRID 1917375 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:19][C@:18]2([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCCCC>C(O)(C)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:19][C:18]2([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:13]([CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8058HexaneHCID 67491042HCID 67491042, compound

Product 1

HCID 67491040HCID 67491040, compoundYield 6.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The racemate (1R*,6S*)-8-benzyloxycarbonyl-1-tert-butoxycarbonylamino-8-azabicyclo[4.3.0]nonane (6.65 g, 17.8 mmol) was optically resolved by an optically active column (CHIRALPAK AD, 20 mm diameter×250 mm, hexane:isopropyl alcohol=95:5, flow rate=20 ml/min) to give optically active 8-benzyloxycarbonyl-1-tert-butoxycarbonylamino-8-azabicyclo[4.3.0]nonane (optical isomer A) (427 mg, 1.14 mmol, retention time=14.2 min) and its optically active enantiomer 8-benzyloxycarbonyl-1-tert-butoxycarbonylamino-8-azabicyclo[4.3.0]nonane (optical isomer B) (415 mg, 1.11 mmol, retention time=19.4 min).

Sources & evidence

ORD record
ord-d1422b3424f940a5a90c51845184273d
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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