Cyclohexane → HCID 69266098, compound

HRID 1394935Notes

Reaction equation

HRID 1394935 reaction equation
[Li]C(CC)C.[CH2:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[Si:12]([O:19][C@@H:20]1[CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:22]([C:32]2C=CC=CC=2)[CH2:21]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].FC(F)(F)S(OC)(=O)=O>C1COCC1>[Si:12]([O:19][C@@H:20]1[CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@:22]([CH3:32])([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:21]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 8078CyclohexaneHCID 9526Methyl triflateHCID 450370281,1-Dimethylethyl (2S,4S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-phenyl-1-pyrrolidinecarboxylateHCID 178418400CID 53628100

Product 1

HCID 69266098HCID 69266098, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of sec-BuLi in cyclohexane (1.4 M, 2.65 mL, 3.71 mmol, 1.40 equiv) was added to a solution of tertramethylethylenediamine (0.880 mL, 5.83 mmol, 2.20 equiv) and tert-butyl(2S,4S)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-phenylpyrrolidine-1-carboxylate (5-1, 1.00 g, 2.65 mmol, 1 equiv) in THF (150 mL) at −78° C. The resulting bright yellow mixture was stirred for 1 hour, then methyl trifluoromethanesulfonate (1.20 mL, 10.6 mmol, 4.00 equiv) was added. The mixture was warmed to 0° C. and stirred for 30 minutes, then partitioned between saturated sodium chloride solution (100 mL) and ethyl acetate (2×75 mL). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (hexanes, grading to 50% ethyl acetate in hexanes) to provide tert-butyl(2S,4S)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-2-phenylpyrrolidine-1-carboxylate (21-1) as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.38-7.18 (m, 5H), 4.39 (m, 1), 3.92 (dd, 1H, J=10.8, 5.1 Hz), 3.65 (br d, 1H, J=10.8 Hz), 2.28 (dd, 1H, J=13.0, 4.5 Hz), 2.13 (br d, 1H, J=12.8 Hz), 1.92 (s, 3H), 1.12 (s, 9H), 0.91 (s, 9H), 0.03 (s, 3H), 0.02 (s, 3H). LRMS m/z (M+H-Boc) 292.2 found, 292.2 required.

Workup

  1. stirringstirred for 30 minutes
  2. custompartitioned between saturated sodium chloride solution (100 mL) and ethyl acetate (2×75 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (hexanes, grading to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-becab84035aa4deda0866e812575e30c
Source dataset
uspto-grants-2008_03
Patent number
US07348440B2

Reaction notes

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