Lithium Hydroxide → HCID 69360553, compound

HRID 1269091Notes

Reaction equation

HRID 1269091 reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][C:9]([F:14])([CH2:11][CH2:12][CH3:13])[CH2:8][CH2:7][N:6]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:4].[OH-].[Li+]>O1CCOCC1.O>[C:18]([O:17][C:15]([N:6]1[CH2:7][CH2:8][C:9]([F:14])([CH2:11][CH2:12][CH3:13])[CH2:10][CH:5]1[C:3]([OH:4])=[O:2])=[O:16])([CH3:19])([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 69914526HCID 69914526, compound

Product 1

HCID 69360553HCID 69360553, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A stirred solution of 21c (m=2, P2=Boc, R9=n-propyl) (1.06 g, 3.47 mmol) in dioxane-water 6:1 (42 mL) was treated with 1.0 M aq. lithium hydroxide (5.3 mL, 5.3 mmol). The reaction mixture was stirred at room temperature overnight, then treated with additional 1.0 M aq. lithium hydroxide (1.5 mL) and the resulting reaction mixture was stirred 5 h. The reaction solvent was removed, the residue was taken up in ethyl acetate (500 mL), washed with 10% Citric acid and brine and dried over MgSO4. Concentration of organic solution to afford the desired product 4-fluoro-4-propyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 21d (m=2, P2=Boc, R9=n-propyl) (0.88 g, 87%) as a white solid.

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred 5 h
  3. customThe reaction solvent was removed
  4. washwashed with 10% Citric acid and brine
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-15c59a40cf2749449c80d2eec8e1ff84
Source dataset
uspto-grants-2007_04
Patent number
US07199105B2

Reaction notes

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