Diisopropylethylamine → HCID 86642506, compound

HRID 2273779Notes

Reaction equation

HRID 2273779 reaction equation
[NH:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.[F:14][CH:15]([F:18])[CH2:16]I.C(N(C(C)C)C(C)C)C>CN(C)C=O>[F:14][CH:15]([F:18])[CH2:16][N:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:2]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 38335651,1-Difluoro-2-iodoethane

Product 1

HCID 86642506HCID 86642506, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (R)-tert-butyl pyrrolidin-3-ylcarbamate (500 mg), 1,1-difluoro-2-iodoethane (618 mg) in N,N-dimethylformamide (6 mL) was added N-ethyl-N-isopropylpropan-2-amine (1.403 mL) and the reaction stirred for 72 hours at 70° C. The reaction mixture was concentrated and the crude product was purified on a silica gel and was eluted with a 0, 2, and 5% methanol in methylene chloride step gradient to provide the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude product was purified on a silica gel
  3. washwas eluted with a 0, 2, and 5% methanol in methylene chloride step gradient

Sources & evidence

ORD record
ord-cce5f345758841a3a10765c68579c9f1
Source dataset
uspto-grants-2015_09
Patent number
US09125913B2

Reaction notes

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