Triethylamine → HCID 59853010, compound

HRID 2374087Notes

Reaction equation

HRID 2374087 reaction equation
[N:1]1([C@@H:6]2[CH2:10][NH:9][CH2:8][C@H:7]2[OH:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:13]([CH3:17])([CH3:16])[C:14]#[CH:15].CCN(CC)CC>[Cu]I.C1COCC1>[CH3:16][C:13]([N:9]1[CH2:10][C@@H:6]([N:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[C@H:7]([OH:11])[CH2:8]1)([C:14]#[CH:15])[CH3:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 706791-Butyne, 3-chloro-3-methyl-HCID 59152451rel-(3′R,4′R)-[1,3′-Bipyrrolidin]-4′-ol

Product 1

HCID 59853010HCID 59853010, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (3R,4R)-4-(pyrrolidin-1-yl)pyrrolidin-3-ol (Lexicon Pharma, 1.56 g, 10.0 mmol) and 3-chloro-3-methyl-1-butyne (GFS Chmeical, Inc., 1.36 g, 13.2 mmol), THF (15 mL) and Et3N (13.3 mmol) was treated with CuI (77 mg, 0.78 mmol). An exothermic reaction ensued with concomitant formation of a precipitate. After stirring at RT for 15 h, the mixture was concentrated in vacuo and partitioned between EtOAc and saturated aqueous NaHCO3 solution. The aqueous phase was extracted twice with EtOAc and the combined EtOAc phases were dried (MgSO4) and concentrated to give a light brown solid (1.0 g, 45%). 1H NMR (CDCl3) δ 4.20 (br s, 1H), 3.13-3.04 (m, 1H), 2.95 (dd, 1H, J=10.1, 6.6 Hz), 2.77 (dd, 1H, J=10.1, 2.6 Hz), 2.64 (m, 3H), 2.61 (m, 2H), 2.55-2.46 (m, 1H), 2.26 (s, 1H), 1.85-1.74 (m, 4H), 1.38 (s, 3H), 1.36 (s, 3H); MS(ESI+): m/z 223.29 (M+H)+.

Workup

  1. customAn exothermic reaction
  2. concentrationthe mixture was concentrated in vacuo
  3. custompartitioned between EtOAc and saturated aqueous NaHCO3 solution
  4. extractionThe aqueous phase was extracted twice with EtOAc
  5. dry with materialthe combined EtOAc phases were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0545acfad13d4d93b2ca9c2f70f53e88
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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