Triethylamine → HCID 66658730, compound

HRID 421215Notes

Reaction equation

HRID 421215 reaction equation
[C@@H:1]1([CH2:10][OH:11])[NH:6][CH2:5][CH2:4][N:3]2[CH2:7][CH2:8][CH2:9][C@@H:2]12.C(N(CC)CC)C.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>C(Cl)Cl.O>[CH3:23][C:22]([Si:19]([CH3:21])([CH3:20])[O:11][CH2:10][C@@H:1]1[NH:6][CH2:5][CH2:4][N:3]2[CH2:7][CH2:8][CH2:9][C@@H:2]12)([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 66658602HCID 66658602, compound

Product 1

HCID 66658730HCID 66658730, compoundYield 56.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of cis-Octahydropyrrolo[1,2-a]pyrazin-1-ylmethanol (D72, 198 mg) in anhydrous DCM (10 mL) under a Nitrogen atmosphere at room temperature, triethylamine (350 microL) and t-butyldimethylsilylchloride (286 mg) were added. The resulting solution was stirred at room temperature overnight then diluted with water (5 mL). The aqueous phase was extracted with DCM (2×10 mL). The combined organic extracts were dried and concentrated in vacuo to a residue which was purified by flash chromatography (DCM/0.5M NH3 in MeOH from 100/0 to 90/10) to give the desired compound (195 mg) as yellow oil.

Workup

  1. extractionThe aqueous phase was extracted with DCM (2×10 mL)
  2. customThe combined organic extracts were dried
  3. concentrationconcentrated in vacuo to a residue which
  4. customwas purified by flash chromatography (DCM/0.5M NH3 in MeOH from 100/0 to 90/10)

Sources & evidence

ORD record
ord-3f733a758cc248289d0751927daa735e
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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