Benzylamine → tert-Butyl (3R,4R)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate

HRID 1670617Notes

Reaction equation

HRID 1670617 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([OH:13])[C@H:10](Br)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>[OH-].[Na+]>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([OH:13])[C@H:10]([NH:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 73553706rel-1,1-Dimethylethyl (3R,4R)-3-bromo-4-hydroxy-1-pyrrolidinecarboxylate

Product 1

HCID 25219891tert-Butyl (3R,4R)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

Stir a mixture of crude rac-trans-3-bromo-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (75.0 g) and aqueous 1 N sodium hydroxide (400 mL) at room temperature for 2 h. Add benzylamine (0.86 mol, 80.0 g,), stir at 65° C. for 4.5 h and then cool to 0° C. Collect the resultant precipitates by filtration, wash with water and isopropyl ether and dry to obtain the title compound as a white solid (50.0 g, 63%). 1H NMR (300 MHz, CDCl3) δ 7.21-7.38 (m, 5H), 4.06-4.15 (m, 1H), 3.84 (d, J=5.0 Hz, 2H), 3.57-3.75 (m, 2H), 3.10-3.35 (m, 3H), 1.65 (br s, 2H), 1.46 (s, 9H).

Workup

  1. customCollect the resultant
  2. customprecipitates by filtration
  3. washwash with water and isopropyl ether
  4. customdry

Sources & evidence

ORD record
ord-47c53db85b7541c6b10eeb3fa4429a76
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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