Triethylamine → HCID 66565985, compound

HRID 926714Notes

Reaction equation

HRID 926714 reaction equation
Br[CH2:2][CH2:3][OH:4].[NH:5]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6]1.CCN(CC)CC>C(#N)C.CCOC(C)=O>[OH:4][CH2:3][CH2:2][N:5]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])[CH2:6]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 108982-BromoethanolHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine

Product 1

HCID 66565985HCID 66565985, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromoethanol (338 mg, 2.703 mmol) was added to a solution of (S)-tert-butyl pyrrolidin-3-ylcarbamate (500 mg, 2.7 mmol) and Et3N (328 mg, 3.24 mmol) in acetonitrile (5 mL) in a seal tube and stirring was continued at 60° C. for 32 h. Reaction mixture was concentrated under reduced pressure to afford the crude, which was diluted with EtOAc, washed it with water followed by brine solution and dried over anhydrous sodium sulphate, concentrated under reduced pressure to afford 430 mg of the title compound.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customto afford the crude, which
  4. washwashed it with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-05fb2ebd0498415d8306f2e99614b2d2
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

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