Triethylamine → HCID 86677331, compound

HRID 1842712Notes

Reaction equation

HRID 1842712 reaction equation
C(Br)(Br)(Br)Br.[CH2:6]([NH:13][CH2:14][C:15]1([CH2:27]O)[CH2:19][CH2:18][CH2:17][N:16]1[C:20]([O:22][C:23]([CH3:26])(C)C)=[O:21])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:29]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:30]=1.C(N(CC)CC)C>C(Cl)Cl.CC#N>[CH2:6]([N:13]1[CH2:14][C:15]2([CH2:19][CH2:18][CH2:17][N:16]2[C:20]([O:22][CH2:23][CH2:26][CH2:29][CH3:30])=[O:21])[CH2:27]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 71241132HCID 71241132, compound2×

Product 1

HCID 86677331HCID 86677331, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of CBr4 (369.5 g, 1.115 mol) in 1 L of CH2Cl2 was added dropwise to a solution of tert-butyl 2-[(benzylamino)methyl]-2-(hydroxymethyl)pyrrolidine-1-carboxylate (Intermediate 51, 178.5 g, 555 mmol) and triphenylphosphine (292 g, 1.115 mol) in CH2Cl2 (1.8 L) at 0° C. The resulting mixture was stirred at r.t. for 2 h then concentrated in vacuo. The residue was suspended in a mixture of CH3CN (2 L) and triethylamine (563.5 g, 5.57 mol) and refluxed at 80° C. for 24 h. The mixture was then concentrated in vacuo. Purification by FCC, eluting with 1:1 petrol-EtOAc gave the title compound (97.5 g, 58%) as yellow oil; 1H NMR: (300 MHz, CDCl3) 1.47-1.72 (11H, m), 2.30 (2H, m), 3.19 (2H, d), 3.31-3.47 (2H, m), 3.82-4.12 (4H, m), 7.22-7.28 (5H, m).

Workup

  1. concentrationthen concentrated in vacuo
  2. temperaturerefluxed at 80° C. for 24 h
  3. concentrationThe mixture was then concentrated in vacuo
  4. customPurification by FCC
  5. washeluting with 1:1 petrol-EtOAc

Sources & evidence

ORD record
ord-7b6e913701a940c7a708142cc2b699d1
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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