Hydrochloric Acid → HCID 13042967, compound

HRID 1435348Notes

Reaction equation

HRID 1435348 reaction equation
[CH3:1][S:2]([N:5]1[CH2:11][CH2:10][CH:9]2[CH:7]([O:8]2)[CH2:6]1)(=[O:4])=[O:3].[Br-:12].[Li+].Cl>O1CCCC1.[Cu](Br)Br>[Br:12][CH:9]1[CH2:10][CH2:11][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6][CH:7]1[OH:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 82050Lithium BromideHCID 13042966HCID 13042966, compound

Product 1

HCID 13042967HCID 13042967, compound

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the epoxide (177 mg, 1 mmol, Example 303) in tetrahydrofuran (8 mL), lithium bromide (543 mg, 6.25 mmol, Aldrich) and copper(II)bromide (725 mg, 3.25 mmol, Aldrich) were added and the mixture was stirred at room temperature overnight. The mixture was poured into 0.1N hydrochloric acid (33 mL) and extracted with ethyl acetate (3×10 mL). The extracts were combined, washed with water, brine and dried with MgSO4. The solvent was removed to give the desired product as colorless oil after passing through an aluminum column (eluted with 5% methanol/dichloromethane). 237 mg, 92%. H1NMR (300 MHz, CDCl3), ppm: 2.00-2.20 (m), 1 H; 2.38-2.52 (m), 1 H; 2.70 (br), 1 H (OH); 2.99 (s), 3H; 3.0-3.20 (m), 2 H; 3.50-3.51 (m), 1 H; 3.80-3.97 (m), 2 H; 4.0-4.10 (m), 1 H. The compound was used directly for the next step.

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washwashed with water, brine
  3. dry with materialdried with MgSO4
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-02ff125a184b4d17bc63c6dbef7a2fe6
Source dataset
uspto-grants-2009_11
Patent number
US07615634B2

Reaction notes

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