Sodium borohydride → Tert-butyl 5-cyclopropyl-2-fluoro-4-((4-hydroxybicyclo-[4.1.0]heptan-1-yl)methoxy)benzoate

HRID 1849838Notes

Reaction equation

HRID 1849838 reaction equation
[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]34[CH2:26][CH:25]3[CH2:24][C:23](=[O:27])[CH2:22][CH2:21]4)=[CH:6][C:7]([F:17])=[C:8]([CH:16]=2)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][CH2:2]1.[BH4-].[Na+]>COCCOC>[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]34[CH2:26][CH:25]3[CH2:24][CH:23]([OH:27])[CH2:22][CH2:21]4)=[CH:6][C:7]([F:17])=[C:8]([CH:16]=2)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86703724Tert-butyl 5-cyclopropyl-2-fluoro-4-((4-oxobicyclo[4.1.0]heptan-1-yl)methoxy)benzoate

Product 1

HCID 86703725Tert-butyl 5-cyclopropyl-2-fluoro-4-((4-hydroxybicyclo-[4.1.0]heptan-1-yl)methoxy)benzoateYield 20.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of tert-butyl 5-cyclopropyl-2-fluoro-4-((4-oxobicyclo[4.1.0]heptan-1-yl)methoxy)benzoate (0.63 g, 1.70 mmol) was dissolved in 1,2- dimethoxyethane (5 mL), sodium borohydride (0.13 g, 3.40 mmol) was added. The reaction mixture was stirred for 0.5 hour and quenched with slow addition of water (5 mL) followed by ethyl acetate (10 mL). To this reaction mixture was added concentrated hydrochloride (37%, 1.0 mL) and stirred for 10 minutes. The organic layer was separated and the solvent was concentrated in vacuo to afford the title compound as a solid (0.13 g, 19%): 1H NMR (300 MHz, CDCl3) (7.36 (d, J=8.5 Hz, 1H), 6.40 (d, J=12.7 Hz, 1H), 3.78 (d, J=9.2 Hz, 1H), 3.62 (d, J=9.4 Hz, 1H), 2.40-2.30 (m, 4H), 2.20-2.07 (m, 2H), 1.99-1.92 (m, 1H), 1.53 (s, 9H), 1.42-1.33 (m, 1H), 1.29-1.09 (m, 2H), 0.89-0.82 (m, 4H), 0.76-0.71 (m, 1H, 0.65-0.60 (m, 2H), 0.47 (t, J=5.3 Hz, 1H); MS (ES+) m/z 377.2 (M+1).

Workup

  1. customquenched with slow addition of water (5 mL)
  2. additionTo this reaction mixture was added concentrated hydrochloride (37%, 1.0 mL)
  3. stirringstirred for 10 minutes
  4. customThe organic layer was separated
  5. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-6f5a92c37cce45e9990b9a8b90eba3c3
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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