Sodium Hydroxide → HCID 58226374, compound

HRID 1614853Notes

Reaction equation

HRID 1614853 reaction equation
[CH3:1][O:2][CH:3]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:4][C@H:5]1[O:8][C:7](=[O:9])[CH2:6]1.[OH-:19].[Na+]>C1COCC1.O>[OH:8][C@H:5]([CH2:4][CH:3]([O:2][CH3:1])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:6][C:7]([OH:19])=[O:9]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58226385HCID 58226385, compound

Product 1

HCID 58226374HCID 58226374, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(ref. Gu, et al. Nature 459, 731-735 (2009)). To a solution of 6 (92.0 mg, 0.359 mmol, 1.0 equiv) in THF (1.5 mL) was added a solution of NaOH (15.7 mg, 0.394 mmol, 1.1 equiv) in water (1.5 mL). The reaction mixture was stirred at rt for 1 h. During this time, its appearance changed from turbid to clear (t=about 0.5 h). The solution was quenched by addition of 1 M HCl (1 mL) and extracted with ether (2×5 mL). The combined organic layers were washed with water (5 mL) and brine (5 mL), dried (Na2SO4) and concentrated in vacuo to afford a pale yellow oil. Purification of the crude product by chromatography on SiO2 (1:1 EtOAc/hexanes containing 0.5% AcOH) provided (3R)-1 (94.4 mg, 96%) as a colorless oil: ATR/IR 2920, 2851, 1709, 1413, 1187, 1079, 736 cm−1; 1H NMR (CDCl3) 4.35-4.20 (m, 1H), 3.55-3.45 (m, 1H), 3.38, 3.37 (2s, 3H), 2.56-2.50 (m, 2H), 1.80-1.35 (m, 3H), 1.35-1.25 (m, 14H), 0.90 (t, 3H, J=6.9 Hz); 13C NMR (CDCl3) 176.4, 175.7, 68.1, 65.4, 56.7, 56.0, 41.6, 41.5, 39.7, 39.1, 32.9, 32.8, 31.9, 29.8, 29.6, 29.5, 29.3, 25.2, 24.5, 22.7, 14.1.

Workup

  1. customchanged from turbid to clear (t=about 0.5 h)
  2. customThe solution was quenched by addition of 1 M HCl (1 mL)
  3. extractionextracted with ether (2×5 mL)
  4. washThe combined organic layers were washed with water (5 mL) and brine (5 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customto afford a pale yellow oil
  8. customPurification of the crude product by chromatography on SiO2 (1:1 EtOAc/hexanes containing 0.5% AcOH)
  9. customprovided (3R)-1 (94.4 mg, 96%) as a colorless oil

Sources & evidence

ORD record
ord-9f347cb7b4004457ab88b6fd705742f8
Source dataset
uspto-grants-2014_07
Patent number
US08765431B2

Reaction notes

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