Benzylamine → HCID 45275492, compound

HRID 1667068Notes

Reaction equation

HRID 1667068 reaction equation
[O:1]=[C:2]1[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][N:3]1[CH2:19][C:20](O)=[O:21].C(N(C(C)C)CC)(C)C.[C:32]1([CH2:38][NH2:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>ClCCl>[CH2:38]([NH:39][C:20](=[O:21])[CH2:19][N:3]1[CH2:4][CH2:5][C:6]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:2]1=[O:1])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 45275492HCID 45275492, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.031 g, 0.105 mmol) and 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.044 g, 0.115 mmol) in dichloromethane (0.5 mL) was added diisopropylethylamine (0.027 mL, 0.157 mmol) followed by phenylmethanamine (0.014 mL, 0.126 mmol). After stirring overnight, the reaction was loaded onto a silica gel column (Analogix® SF15-12, Burlington, Wis.), and the product was eluted with a gradient of 0.4% to 5.25% methanol/dichloromethane over 20 minutes with a flow rate of 30 mL/minute. The product residue was dissolved in dichloromethane/diethyl ether followed by the addition of hexanes which upon concentration gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.11-7.34 (m, 15H), 6.23 (t, J=5.8 Hz, 1H), 4.32 (d, J=5.8 Hz, 2H), 4.06 (s, 2H), 3.50 (t, J=6.5 Hz, 2H), 2.80 (t, J=6.5 Hz, 2H); MS (ESI−) m/z 383 (M−H)−.

Workup

  1. washthe product was eluted with a gradient of 0.4% to 5.25% methanol/dichloromethane over 20 minutes with a flow rate of 30 mL/minute
  2. dissolutionThe product residue was dissolved in dichloromethane/diethyl ether
  3. additionfollowed by the addition of hexanes which upon concentration

Sources & evidence

ORD record
ord-49ac901e73b04265866e12e5a9b127d4
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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