Sodium Hydroxide → Tert-butyl 3-(3,5-dichlorophenyl)pyrrolidine-1-carboxylate

HRID 1098665Notes

Reaction equation

HRID 1098665 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:11](OC)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[BH4-].[Na+].[OH-].[Na+]>C(O)(=O)C>[C:17]([O:16][C:14]([N:12]1[CH2:11][CH2:10][CH:9]([C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH2:13]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 59593456Tert-butyl 4-(3,5-dichlorophenyl)-2-methoxypyrrolidine-1-carboxylate

Product 1

HCID 59593447Tert-butyl 3-(3,5-dichlorophenyl)pyrrolidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Synthesized according to General procedure 3. To a stirred solution of tert-butyl 4-(3,5-dichlorophenyl)-2-methoxypyrrolidine-1-carboxylate (20 g, 0.058 mol) in acetic acid (200 mL) under N2 at 0° C. was added sodium borohydride (4.37 g, 0.116 mol) in portions over 20 minutes. The resulting solution was allowed to warm to RT and then stirred at RT for 1 hour. The reaction mixture was slowly poured into 2 M aqueous NaOH solution (500 mL) and extracted with ethyl acetate (3×500 mL). The combined organic extracts were dried over Na2SO4, filtered through a pad of Celite and then concentrated under reduced pressure to afford tert-butyl-3-(3,5-dichlorophenyl)pyrrolidine-1-carboxylate as a brown oil (18.3 g, 0.058 mol, 100% yield). 1H-NMR (400 MHz, CDCl3) δ 7.28-7.24 (m, 1H), 7.13 (d, J=1.3 Hz, 2H), 3.80-3.76 (m, 1H), 3.65 (t, J=8.4 Hz, 1H), 3.56 (t, J=8.1 Hz, 1H), 3.46-3.39 (m, 1H), 3.35-3.23 (m, 1H), 2.27 (d, J=4.3 Hz, 1H), 2.01-1.93 (m, 1H) and 1.51 (s, 9H) ppm.

Workup

  1. customSynthesized
  2. extractionextracted with ethyl acetate (3×500 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered through a pad of Celite
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-48168e4c2db5404daf5a405b48fed41e
Source dataset
uspto-grants-2012_03
Patent number
US08143297B2

Reaction notes

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