Lithium Hexamethyldisilazide → diisopropyl (2R,3S)-2-(cyclopentylmethyl)-3-hydroxysuccinate

HRID 888217Notes

Reaction equation

HRID 888217 reaction equation
[CH:1]([O:4][C:5](=[O:15])[C@H:6]([CH2:8][C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])[OH:7])([CH3:3])[CH3:2].I[CH2:17][CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[CH:18]1([CH2:17][C@H:8]([C@H:6]([OH:7])[C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[O:15])[C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 2762531(Iodomethyl)cyclopentaneHCID 11333435Diisopropyl (S)-(-)-malate

Product 1

HCID 58488004diisopropyl (2R,3S)-2-(cyclopentylmethyl)-3-hydroxysuccinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

To a cold (5° C.) solution of diisopropyl-(S)-(−)-malate (50.0 g, 229.1 mmol, 1.0 eq.) and (iodomethyl)cyclopentane (55.6 g, 264.6 mmol, 1.15 eq.) in anhydrous THF (250 mL) under N2 was added over a period of 90 min. a solution (1M) of lithium bis(trimethylsilyl)amide (481 mL; 1.0 M, 481.1 mmol, 2.1 eq.) in THF. The temperature was allowed to warm to 20° C. and the mixture was stirred for 15 hours until completion (monitoring by TLC (SiO2); cyclohexane 8-ethyl acetate 2; treated with molibdic acid).

Sources & evidence

ORD record
ord-95b088043d3a47ecb4fd256749eb9ad8
Source dataset
uspto-grants-2012_08
Patent number
US08247437B2

Reaction notes

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