Diisopropylethylamine → HCID 86642506, compound

HRID 1848909Notes

Reaction equation

HRID 1848909 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

(R)-tert-butyl pyrrolidin-3-ylcarbamate (500 mg) was combined with 1,1-difluoro-2-iodoethane (618 mg) and N-ethyl-N-isopropylpropan-2-amine (1.4 mL) in N,N-dimethylformamide (6 mL) in a 20 mL vial. The reaction was heated to 70° C. for 48 hours. The reaction mixture was concentrated and the residue was purified by flash chromatography, eluting with a gradient of 0-5% methanol in dichloromethane to provide the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography
  3. washeluting with a gradient of 0-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-9b1c7962dd3a4b9ca962c7ef225192f8
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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