(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine → HCID 86673373, compound

HRID 535807Notes

Reaction equation

HRID 535807 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[CH:13][C:12]([C@@H:25]2[CH2:27][C@H:26]2[NH:28][CH2:29][CH2:30]Cl)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:32]1[CH2:36][CH2:35][C@@H:34]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:33]1>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[CH:13][C:12]([C@@H:25]2[CH2:27][C@H:26]2[NH:28][CH2:29][CH2:30][N:32]2[CH2:36][CH2:35][C@@H:34]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:42])([CH3:41])[CH3:43])[CH2:33]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 67065023HCID 67065023, compound

Product 1

HCID 86673373HCID 86673373, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (trans)-2-(6-(benzyloxy)-4′-(trifluoromethyl)biphenyl-3-yl)-N-(2-chloroethyl)cyclopropanamine (500 mg, 1.12 mmol) in dry DMF (5 mL), (R)-tert-butyl pyrrolidin-3-ylcarbamate (438 mg, 2.3 mmol) was added and stirred at RT for 48 h. After completion, the reaction mixture was poured into ice water (20 mL), extracted with EtOAc (2×20 mL). The combined extracts were washed with water (25 mL), brine, dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purified by column chromatography (SiO2) using MeOH: CHCl3 (4:96) to get tert-butyl(R)-1-(2-((trans)-2-(6-(benzyloxy)-4′-(trifluoromethyl)biphenyl-3-yl)cyclopropylamino)ethyl)pyrrolidin-3-ylcarbamate (400 mg, 60.6%) as a white solid.

Workup

  1. extractionextracted with EtOAc (2×20 mL)
  2. washThe combined extracts were washed with water (25 mL), brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude residue was purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-832ab1e2aa9946799a0ed55f6c164ea5
Source dataset
uspto-grants-2014_10
Patent number
US08859555B2

Reaction notes

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