Pivaloyl chloride → (S)-3-(2',2'-Dimethyl-1'-oxopropyl)-4,5,5-trimethyloxazolidin-2-one

HRID 2392835Notes

Reaction equation

HRID 2392835 reaction equation
[CH3:1][C@H:2]1[C:6]([CH3:8])([CH3:7])[O:5][C:4](=[O:9])[NH:3]1.C([Li])CCC.[C:15](Cl)(=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17]>O1CCCC1>[CH3:17][C:16]([CH3:19])([CH3:18])[C:15]([N:3]1[C@@H:2]([CH3:1])[C:6]([CH3:8])([CH3:7])[O:5][C:4]1=[O:9])=[O:20]

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 11073445(S)-4,5,5-Trimethyloxazolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 18664915(S)-3-(2',2'-Dimethyl-1'-oxopropyl)-4,5,5-trimethyloxazolidin-2-oneYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of the auxiliary (5) (0.180 g, 1.40 mmol) in solution in tetrahydrofuran (3 ml) at -78° C. with butyllithium (1.4M, 1 ml, 1.41 mmol) and pivaloyl chloride (0.190 ml, 1.55 mmol) for 30 minutes and then at room temperature for 1 hour with work-up and recrystallisation at ca -10° C. from 60-80 petroleum ether furnished the title compound (16) as a solid (0.276 g, 93%); νmax (CH2Cl2) 1683 and 1775 cm-1 ; [α]D24 (c 1 in CHCl3)=+51.3; (Found: C, 62.25; H, 9.09; N, 6.45. C11H19NO3 requires C, 61.95; H, 8.98; N, 6.57%); δH (CDCl3 ; 300 MHz) 1.20 (3H, d, J=6.5, CH3CH), 1.31 (9H, s, C(CH3)3), 1.33 (3H, s, C(CH3)2), 1.37 (3H, s, C(CH3)2), 4.11 (1H, q, J=6.5, CHCH3) ; δC (125 MHz; CDCl3) 14.33 (CH3), 21.41 (CH3), 26.31 (CH3), 27.22 (CH3), 41.60 (CH3), 60.92 (CH), 81.01 (C), 151.75 (CO), 179.08 (CO); m/z (CI+, NH3) 214 (M+ +1).

Workup

  1. customat room temperature for 1 hour with work-up and recrystallisation at ca -10° C. from 60-80 petroleum ether

Sources & evidence

ORD record
ord-6e042cd72a1948d1a40c70c3a1286b1c
Source dataset
uspto-grants-1998_09
Patent number
US05801249

Reaction notes

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