1-Boc-3-aminopyrrolidine → HCID 91465771, compound

HRID 2191094Notes

Reaction equation

HRID 2191094 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[C:17]([C:19]3[C:23]4[CH2:24][C:25]([CH3:30])([CH3:29])[CH2:26][C:27](=[O:28])[C:22]=4[S:21][C:20]=3[N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[CH:16]=[CH:15][N:14]=2)[CH:8]=1)(=O)=O.[NH2:39][CH:40]1[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:41]1.CC(C)([O-])C.[K+]>O1CCOCC1.CC(O)=O.CC(P(C(C)(C)C)C1C(C2[C-]=CC=CC=2)=CC=CC=1)(C)C.[Pd]>[CH3:29][C:25]1([CH3:30])[CH2:24][C:23]2[C:19]([C:17]3[CH:16]=[CH:15][N:14]=[C:13]([C:9]4[CH:8]=[C:7]([NH:39][CH:40]5[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:41]5)[CH:12]=[CH:11][CH:10]=4)[CH:18]=3)=[C:20]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[S:21][C:22]=2[C:27](=[O:28])[CH2:26]1

Participants

6

Reactant 3

HCID 27563701-Boc-3-aminopyrrolidineHCID 23665647Potassium tert-butoxideHCID 87571193HCID 87571193, compound

Product 1

HCID 91465771HCID 91465771, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 119822622-(2'-Di-tert-butylphosphine)biphenylpalladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of Example 360 (115 mg, 0.20 mmol), 3-amino-1-(tert-butoxy-carbonyl)pyrrolidine (76 mg, 0.41 mmol), potassium tert-butoxide (32 mg, 0.28 mmol) and acetato(2′-di-tert-butylphosphino-1,1′-biphenyl-2-yl)palladium(II) (20 mg, 0.043 mmol) in 1,4-dioxane (2.0 mL) was heated in a sealed tube at 100° C., under microwave irradiation, for 2 h. The solvent was removed in vacuo and the residue was purified by column chromatography (SiO2, 0-100% EtOAc/heptane) to give the title compound (79 mg, 65%) as an off-white solid. δH (CDCl3) 8.73 (1H, d, J 5.1 Hz), 7.75 (1H, s), 7.38 (1H, s), 7.35-7.23 (3H, m), 6.74-6.68 (1H, m), 4.25-4.12 (1H, m), 4.00-3.88 (1H, m), 3.84-3.73 (1H, m), 3.72-3.64 (4H, m), 3.58-3.43 (2H, m), 3.37-3.20 (1H, m), 3.07-2.99 (4H, m), 2.53 (2H, s), 2.45 (2H, s), 2.31-2.17 (1H, m), 2.01-1.89 (1H, m), 1.47 (9H, s), 1.05 (6H, s). LCMS (ES+) 603.2 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography (SiO2, 0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-9fd556ee295e474783ef80574e2954f9
Source dataset
uspto-grants-2012_12
Patent number
US08324204B2

Reaction notes

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