Tetrahydrofuran → HCID 86596637, compound

HRID 901461Notes

Reaction equation

HRID 901461 reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][C:9]([F:14])([CH2:11][CH2:12][CH3:13])CC[N:6]1[C:15](OC(C)(C)C)=O)=[O:4].O.[OH-].[Li+].[CH2:25]1COCC1>O>[F:14][C:9]1([CH2:11][CH2:12][CH2:13][CH3:25])[CH2:15][NH:6][C@H:5]([C:3]([OH:2])=[O:4])[CH2:10]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 69914526HCID 69914526, compound

Product 1

HCID 86596637HCID 86596637, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 12c (0.27 g, 0.89 mmol) in THF (10 mL) and water (3 mL) was added lithium hydroxide monohydrate (45 mg, 1.06 mmol). The reaction mixture was stirred at room temperature overnight. THF was removed and the residue was purified by column chromatography using 10% MeOH in DCM as eluant to obtain 4-Fluoro-4-butylproline 12d (P=Boc, m=1, R9=n-butyl) (0.26 g, 100%) as a colorless oil: 1H NMR (300 MHz, CD3OD) δ 4.30 (m, 1), 3.72 (m, 1), 3.49 (m, 1), 3.39 (m, 1), 2.58 (m, 1), 2.02 (m, 2), 1.72 (m, 13), 0.93 (t, J=6.6, 3); MS (ESNEG): 288 [M−1]−.

Workup

  1. customTHF was removed
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-dcfeb718b0294b969d0604a0c58fac5c
Source dataset
uspto-grants-2008_04
Patent number
US07361743B2

Reaction notes

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