Sodium Bicarbonate → HCID 9824260, compound

HRID 380505Notes

Reaction equation

HRID 380505 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[C@H:10]([CH:18]=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[CH2:1]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[C@H:10]([CH2:18][N:30]2[CH2:31][CH2:32][CH:27]([C:24]3[CH:23]=[CH:22][C:21]([F:20])=[CH:26][CH:25]=3)[CH2:28][CH2:29]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 27591364-(4-Fluorophenyl)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 20694317HCID 20694317, compound

Product 1

HCID 9824260HCID 9824260, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1.0 g (16.4 mmol) of 1-benzyl-3-(S)-formyl-4-(R)-(3-thienyl)pyrrolidine and 2.94 g (23.4 mmol) of 4-(4-fluorophenyl)piperidine in 50 mL of 1,2-dichlorethane was added 4.96 g (23.4 mmol) of sodium triacetoxyborohydride and the solution was stirred at rt for 16 h. The reaction was poured into 50 mL of saturated NaHCO3 solution and the mixture was extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography (silica, acetone:hexanes, 1:3) to afford the title compound. 1H NMR (CDCl3) δ6.97-7.10 (m, 4H), 3.72 (d, 1H, J=13.1 hz), 3.64 (d, 1H, J=13.0 Hz), 3.11-3.14 (m, 1H); Mass Spectrum (ESI) m/e 435 (M+1); [α]D=−13.3 (c.=0.06, CHCl3)

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (silica, acetone:hexanes, 1:3)

Sources & evidence

ORD record
ord-cd764209b5a04d42b79129d13649d9c1
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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