Lithium Hydroxide → HCID 86675866, compound

HRID 1895772Notes

Reaction equation

HRID 1895772 reaction equation
[OH-:1].[Li+].CC1(C)C2CC[C@@]31[C@H](C2)N([C:14](=[O:24])[C@H:15]([CH3:23])[C@H:16]([O:21][CH3:22])[CH2:17][CH2:18][CH:19]=[CH2:20])S(=O)(=O)C3>O.O1CCCC1>[CH3:22][O:21][C@H:16]([CH2:17][CH2:18][CH:19]=[CH2:20])[C@@H:15]([CH3:23])[C:14]([OH:24])=[O:1]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 89949089HCID 89949089, compound

Product 1

HCID 86675866HCID 86675866, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2M lithium hydroxide in water (5 ml) was added to a stirred solution of 10c (223 mg, 0.60 mmol.) in tetrahydrofuran (15 ml). The stirred mixture was heated to 60° C. for 15 hours. The reaction mixture was partially evaporated before adding 2M hydrochloric acid (20 ml). The solution was extracted with ethyl acetate (3×15 ml). The extract was dried over sodium sulfate filtered and evaporated to give a yellow gum (209 mg). The gum was purified on a silica column eluting with 25% ethyl acetate, 75% hexane to yield 10d as a yellow gum (68 mg, 66%). 1H NMR δ (300 MHz NMR, CDCl3) 1.15-1.19 (d, 3H), 1.57-1.67 (m, 2H), 2.11-2.23 (m, 2H), 2.74-2.85 (m, 1H), 3.39-3.42 (s, 3H), 3.45-3.53 (m, 1H), 4.97-5.10 (m, 2H), 5.76-5.91 (m, 1H).

Workup

  1. customThe reaction mixture was partially evaporated
  2. additionbefore adding 2M hydrochloric acid (20 ml)
  3. extractionThe solution was extracted with ethyl acetate (3×15 ml)
  4. dry with materialThe extract was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-5fe9545fb9134485bf7d9c51a30c7eb7
Source dataset
uspto-grants-2013_08
Patent number
US08513184B2

Reaction notes

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