Methyl (S)-3-Boc-2,2-dimethyloxazolidine-4-propanoate → (S)-tert-butyl 4-(2-(1-hydroxycyclopentyl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 451857Notes

Reaction equation

CO[C:3](=[O:20])[CH2:4][CH2:5][C@H:6]1[CH2:10][O:9][C:8]([CH3:12])([CH3:11])[N:7]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[Mg]([CH2:23][CH2:24][CH2:25][CH2:26][Mg]Br)Br>C1COCC1>[OH:20][C:3]1([CH2:4][CH2:5][C@H:6]2[CH2:10][O:9][C:8]([CH3:11])([CH3:12])[N:7]2[C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

Conditions

Temperature: -10 °C

Procedure

The (S)-tert-butyl 4-(3-methoxy-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate (1.02 g, 3.55 mmol, 1.0 equiv) was dissolved in 50 mL of THF and cooled to −10° C. A 1.0 M solution of BrMg(CH2)4MgBr (7.1 mL, 2.0 equiv) was added and the mixture stirred for 2 h. After this time a second portion of BrMg(CH2)4MgBr was added and the mixture stirred for 1 h. The mixture was quenched by addition of saturated NH4Cl and the mixture transferred to a separatory funnel, and the organic layer was washed with brine, then dried over Na2SO4, filtered, and evaporated to provide crude (S)-tert-butyl 4-(2-(1-hydroxycyclopentyl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate.

Workup

stirringthe mixture stirred for 1 h
customThe mixture was quenched by addition of saturated NH4Cl
customthe mixture transferred to a separatory funnel
washthe organic layer was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-a7a03b51564c46f59cb26caebbd11c93
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487108B2

Reaction notes

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