Sodium borohydride → HCID 58900124, compound

HRID 2242869Notes

Reaction equation

HRID 2242869 reaction equation
[Cl:1][C:2]1[N:3]([C:11]2[CH:30]=[CH:29][C:14]([O:15][CH2:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([C:25](OC)=[O:26])[CH2:21][CH2:20]3)=[CH:13][CH:12]=2)[N:4]=[C:5]2[C:10]=1[CH:9]=[CH:8][CH:7]=[CH:6]2.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[N:3]([C:11]2[CH:12]=[CH:13][C:14]([O:15][CH2:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([CH2:25][OH:26])[CH2:21][CH2:20]3)=[CH:29][CH:30]=2)[N:4]=[C:5]2[C:10]=1[CH:9]=[CH:8][CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58900147HCID 58900147, compound

Product 1

HCID 58900124HCID 58900124, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-{3-[4-(3-chloro-indazol-2-yl)-phenoxy]-propyl}-piperidine-4-carboxylate (0.1 g, 0.21 mmol) in THF (10 mL) was added NaBH4 (23 mg, 0.63 mmol) at 0° C. in portions. The reaction mixture was stirred at room temperature for 4 h. After it was quenched with water, the mixture was extracted with ethyl acetate, washed with brine and water, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by a column chromatography on silica gel eluting with 20% ethyl acetate in hexane to the title compound (0.43 g 50%). 1H NMR (400 MHz, CDCl3) δ 7.71(d, J=8.8 Hz, 1H), 7.59-7.56 (m, 3H), 7.37-7.33 (m, 1H), 7.17-7.14 (m, 2H), 7.04 (d, J=8.8 Hz, 2H), 4.10 (t, J=6 Hz, 2H), 3.22 (m, 2H), 3.01 (br d, J=12 Hz, 1H), 2.54 (t, J=6 Hz, 2H), 2.10-1.73 (m, 9H).

Workup

  1. customAfter it was quenched with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with brine and water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by a column chromatography on silica gel eluting with 20% ethyl acetate in hexane to the title compound (0.43 g 50%)

Sources & evidence

ORD record
ord-a6b19ee6bee341ec83b944fc1ce1a74a
Source dataset
uspto-grants-2010_03
Patent number
US07674802B2

Reaction notes

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