Triethylamine → HCID 66845170, compound

HRID 1916415Notes

Reaction equation

HRID 1916415 reaction equation
O[CH2:2][C@H:3]1[C:11]2[C:10]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)=[N:9][CH:8]=[N:7][C:6]=2[CH2:5][CH2:4]1.[F:25]C(F)(S(F)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.F.F.F.C(N(CC)CC)C.C(N(CC)CC)C>O1CCCC1>[C:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][N:12]([C:10]2[C:11]3[C@H:3]([CH2:2][F:25])[CH2:4][CH2:5][C:6]=3[N:7]=[CH:8][N:9]=2)[CH2:13][CH2:14]1)=[O:19])([CH3:23])([CH3:22])[CH3:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 70676617HCID 70676617, compound

Product 1

HCID 66845170HCID 66845170, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-tert-Butyl 4-(5-(hydroxymethyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate (30.0 mg, 0.0897 mmol) was dissolved in tetrahydrofuran (0.080 mL). Perfluoro-1-butanesulfonylfluoride (0.0644 mL, 0.359 mmol) and triethylamine trishydrofluoride (0.0584 mL, 0.359 mmol) were added to this solution, followed by triethylamine (0.150 mL, 0.726 mmol). The reaction mixture was allowed to stir for 12 hours at room temperature. The reaction was concentrated, and the material was subjected to chromatography on SiO2 and eluted with 10% MeOH/DCM. The desired 4-((R)-5-fluoromethyl-6,7-dihydro-5H-cyclopentapyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (25.0 mg, 83%) was isolated. LC/MS (APCI)+ m/z 337.2.

Workup

  1. concentrationThe reaction was concentrated
  2. washeluted with 10% MeOH/DCM

Sources & evidence

ORD record
ord-86c570ac3c12458c9f635df9f9d6d680
Source dataset
uspto-grants-2013_12
Patent number
US08618097B2

Reaction notes

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