(3R)-(+)-3-(Dimethylamino)pyrrolidine → Dimethyl-[1-(5-nitro-benzooxazol-2-yl)-pyrrolidin-3-yl]-amine

HRID 1174917Notes

Reaction equation

HRID 1174917 reaction equation
CS[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:6]=2[N:7]=1.[CH3:15][N:16]([CH3:22])[C@@H:17]1[CH2:21][CH2:20][NH:19][CH2:18]1>C1(C)C=CC=CC=1>[CH3:15][N:16]([CH3:22])[CH:17]1[CH2:21][CH2:20][N:19]([C:3]2[O:4][C:5]3[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:6]=3[N:7]=2)[CH2:18]1

Participants

4

Reactant 2

HCID 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidineHCID 152521182-(Methylthio)-5-nitrobenzo[d]oxazole

Product 1

HCID 68773862Dimethyl-[1-(5-nitro-benzooxazol-2-yl)-pyrrolidin-3-yl]-amineYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Suspend 2-methylsulfanyl-5-nitro-benzooxazole (1.68 g, 7.99 mmol) in toluene (8 mL). Add (3R)-(+)-3-(dimethylamino)pyrrolidine (1.8 mL) and heat to 70° C. overnight. Cool the reaction to room temperature, dilute with toluene (10 mL) and filter. Wash the product with toluene (5 mL) and hexane (10 mL). Dry on the filter flask for 30 min to afford the title compound (1.00 g, 45%). 1H NMR (400 MHz, DMSO-d6): δ 8.03 (d, 1H, J=2.2 Hz), 7.94 (dd, 1H, J=8.6, 2.4 Hz), 7.62 (d, 1H, J=8.8 Hz), 3.81 (dd, 1H, J=10.1, 7.0 Hz), 3.75 (m, 1H), 3.57 (dt, 1H, J=10.0, 7.2 Hz), 3.34 (m, 1H), 2.86 (m, 1H), 2.21-2.13 (m, 7H), 1.87 (m, 1H).

Workup

  1. temperatureCool
  2. customthe reaction to room temperature
  3. filtrationfilter
  4. washWash the product with toluene (5 mL) and hexane (10 mL)
  5. customDry on the filter flask for 30 min

Sources & evidence

ORD record
ord-c224e1c939314fd2bdb938bed4acb9f2
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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