Butyl iodide → HCID 86598518, compound
Reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][O:8][C@H:7]([C:10]([CH3:13])([CH3:12])[CH3:11])[N:6]1[CH:14]=[O:15])=[O:4].I[CH2:17][CH2:18][CH2:19][CH3:20].CN(P(N(C)C)(N(C)C)=O)C.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1.CCOCC>[CH3:1][O:2][C:3]([C@:5]1([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:9][O:8][C@H:7]([C:10]([CH3:11])([CH3:12])[CH3:13])[N:6]1[CH:14]=[O:15])=[O:4]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of (2R,4S)-2-tert-butyl-3-formyloxazolidine-4-carboxylic acid methyl ester (4.6 g, 21.4 mmol) [see D. Seebach, J. D. Aebi, M. Gander-Coquoz and R. Naef, Helv. Chim. Acta., 70, 1194 (1987)] in dry THF (120 mL) under N2 was added 1-iodobutane (12.2 mL, 106.8 mmol) and HMPA (12 mL). The mixture was cooled to −78° C. and a solution of sodium bis(trimethylsilyl)amide in THF (1 M, 32 mL, 32 mmol) was added dropwise over 15 minutes. After 2 h, the reaction mixture was warmed to 0° C. and quenched with saturated aqueous NH4Cl (200 mL). The quenched reaction mixture was diluted with ether (400 mL) and washed with water (3×200 mL) and brine (200 mL), then dried (Na2SO4) and filtered. Concentration of the filtrate and flash chromatography of the residue (20% ethyl acetate/hexanes) provided the title compound as a pale brown solid (4.0 g, 69%). MS(ES) m/e 272 [M+H]+.
Workup
- temperaturethe reaction mixture was warmed to 0° C.
- customquenched with saturated aqueous NH4Cl (200 mL)
- customThe quenched reaction mixture
- washwashed with water (3×200 mL) and brine (200 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
Sources & evidence
- ORD record
- ord-50d8dfd3760f45d5ae82826e18b0a2f3
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745637B2
Reaction notes
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