Triethylamine → HCID 22046653, compound

HRID 1830967Notes

Reaction equation

HRID 1830967 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[C:8]([N+:16]([O-:18])=[O:17])[C:4]=1[C:5]([OH:7])=O.[C:19](Cl)(=[O:23])[C:20](Cl)=O.[N:25]1(CO)C[CH2:28][CH2:27][CH2:26]1.C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl>[N+:16]([C:8]1[CH:9]=[C:10]([O:14][CH3:15])[C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[C:4]=1[C:5]([N:25]1[CH2:26][CH2:27][CH2:28][CH:20]1[CH2:19][OH:23])=[O:7])([O-:18])=[O:17]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 620835HCID 620835, compoundHCID 2331391Pyrrolidinemethanol

Product 1

HCID 22046653HCID 22046653, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A catalytic quantity of DMF (2 drops) was added to a stirred solution of 108 (10 g, 38.9 mmol) and oxalyl chloride (5.87 g, 46.2 mmol) in dry CHCl2 (100 mL) under a nitrogen atmosphere. The reaction mixture was allowed to stir overnight, and the product was used directly in the next stage of the reaction. The newly formed acid chloride was added dropwise to a stirred solution of pyrrolidinemethanol (3.92 g, 38.8 mmol) and anhydrous triethylamine (12.4 mL, 9.8 g, 97.0 mmol) in anhydrous DCM (50 mL) at 0° C. under nitrogen. Once the addition was complete, the reaction mixture was left to warm to room temperature and left to stir overnight. The reaction mixture was washed with 1N HCl (100 mL), water (100 mL), and brine (2×100 mL). The combined organic layers were dried (MgSO4) and the solvent was removed in vacuo to afford 109 (12.1 g, 91%) as a pale yellow oil: Rf=0.39 (silica, EtOAc); [α]21.9D+135° (c=0.1, DCM); IR (neat) 3400, 3105, 2947, 2878, 1652, 1568, 1538, 1455, 1348, 1250, 1195, 1115, 975, 922, 849, 822, 792, 758, 733, 646 cm−1; 1H NMR (270 MHz, CDCl3) δ7.59 (1H, s), 4.46 (2H, d, J=2.93 Hz), 4.07 (3H, s), 4.03 (3H, s), 4.01 (3H, s), 3.89 (3H, t), 3.45-3.29 (2H, m), 2.24-2.17 (2H, m), 2.00-1.84 (2H, m); 13C NMR (67.8 MHz, CDCl3, rotamers) δ165.7, 165.1, 153.3, 149.2, 148.1, 138.8, 122.5, 104.1, 66.4, 65.5, 62.4, 62.3, 61.3, 56.6, 49.2, 49.0, 28.7 24.3; MS (EI) m/z 341 (M+1), 324, 309, 293, 277, 264, 254.

Workup

  1. customthe product was used directly in the next stage of the reaction
  2. additionOnce the addition
  3. waitthe reaction mixture was left
  4. waitleft
  5. stirringto stir overnight
  6. washThe reaction mixture was washed with 1N HCl (100 mL), water (100 mL), and brine (2×100 mL)
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-318ad3ef15d943b1be828df5e0999779
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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