Tert-butyl 2-((1-(4-fluorophenyl)cyclohexyl)methoxy)acetate → 2-((1-(4-Fluorophenyl)cyclohexyl)methoxy)acetic acid

HRID 1506294Notes

Reaction equation

HRID 1506294 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][O:15][CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:14][O:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 66685225Tert-butyl 2-((1-(4-fluorophenyl)cyclohexyl)methoxy)acetate

Product 1

HCID 666856282-((1-(4-Fluorophenyl)cyclohexyl)methoxy)acetic acidYield 96%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 2-((1-(4-fluorophenyl)cyclohexyl)methoxy)acetate (Intermediate I-10B, 100 mg, 0.31 mmol) in TFA (1 mL) was stirred at room temperature for 85 min. TFA was removed in vacuo, and the residue was co-evaporated with ether. The residual oil was dried in vacuo to yield 2-((1-(4-fluorophenyl)cyclohexyl)methoxy)acetic acid (79 mg, 96% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.30-7.43 (2H, m), 6.93-7.17 (2H, m), 3.91 (2H, s), 3.46 (2H, s), 2.13 (2H, d, J=13.55 Hz), 1.60-1.76 (2H, m), 1.55 (3H, dd, J=12.17, 3.64 Hz), 1.26-1.44 (3H, m).

Workup

  1. customTFA was removed in vacuo
  2. customThe residual oil was dried in vacuo

Sources & evidence

ORD record
ord-91df0f4b6c4c43b7bc16a28d4efe8c7b
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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