Sodium Bicarbonate → Tert-butyl 3-(4-chloro-3-methylphenyl)pyrrolidine-1-carboxylate

HRID 1098664Notes

Reaction equation

HRID 1098664 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:10](OC)[CH2:9]2)=[CH:4][C:3]=1[CH3:22].[BH4-].[Na+].C([O-])(O)=O.[Na+]>C(O)(=O)C>[C:16]([O:15][C:13]([N:11]1[CH2:10][CH2:9][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH3:22])[CH:4]=2)[CH2:12]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 59593439Tert-butyl 4-(4-chloro-3-methylphenyl)-2-methoxypyrrolidine-1-carboxylate

Product 1

HCID 59593449Tert-butyl 3-(4-chloro-3-methylphenyl)pyrrolidine-1-carboxylateYield 97.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Synthesized according to General Procedure 3. To a stirred solution of crude tert-butyl 4-(4-chloro-3-methylphenyl)-2-methoxypyrrolidine-1-carboxylate (4.25 g, 13.0 mmol) in acetic acid (50 mL) under N2 at 0° C. was added sodium borohydride (2.2 g, 58.7 mmol) in portions over 20 minutes. The resulting solution was allowed to warm to RT and then stirred at RT for 2 hours. The reaction mixture was slowly poured into saturated aqueous NaHCO3 (250 mL) and extracted with ethyl acetate (3×200 mL). The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure to afford tert-butyl-3-(4-chloro-3-methylphenyl)pyrrolidine-1-carboxylate (3.75 g, 12.67 mmol, 97% yield) as a brown oil. 1H-NMR (400 MHz, DMSO-d6) δ 7.33 (d, J=8.2 Hz, 1H), 7.28 (s, 1H), 7.14-7.03 (m, 1H), 3.68 (t, J=8.8 Hz, 1H), 3.48-3.42 (m, 1H), 3.32-3.10 (m, 3H), 2.30 (s, 3H), 2.17-2.15 (m, 1H), 1.78-1.73 (m, 1H) and 1.42 (s, 9H) ppm.

Workup

  1. customSynthesized
  2. extractionextracted with ethyl acetate (3×200 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0063e64ed2654fe88e18dd46efd39631
Source dataset
uspto-grants-2012_03
Patent number
US08143297B2

Reaction notes

Loading…