1-Boc-3-pyrrolidinol → HCID 71255391, compound

HRID 540273Notes

Reaction equation

HRID 540273 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.Cl[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22](OC(F)(F)F)[CH:23]=2)[N:18]=[C:17]([N:30]2[CH2:36][C:35]3[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=3[S:33](=[O:42])(=[O:41])[CH2:32][CH2:31]2)[CH:16]=1.[CH3:43]C(C)([O-])C.[Na+]>O1CCOCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[O:41]=[S:33]1(=[O:42])[C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[CH2:36][N:30]([C:17]2[CH:16]=[C:15]([O:1][CH:2]3[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]3)[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([CH3:43])[CH:23]=3)[N:18]=2)[CH2:31][CH2:32]1

Participants

7

Reactant 3

HCID 44169391-Boc-3-pyrrolidinolHCID 23676156Sodium t-butoxideHCID 712545694-(4-Chloro-6-(trifluoromethoxy)quinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide

Product 1

HCID 71255391HCID 71255391, compoundYield 5.3%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of tert-butyl 3-hydroxypyrrolidine-1-carboxylate (134.7 mg, 0.72 mmol), 4-(4-bromo-6-methylquinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide (300 mg, 0.72 mmol, prepared in analogy to 4-(4-chloro-6-(trifluoromethoxy)quinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide in Example 17-1), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (57.12 mg, 0.07 mmol), 1,1′-bis(diphenylphosphino)ferrocene (38.78 mg, 0.07 mmol) and sodium tert-butoxide (138.24 mg, 1.44 mmol) in 1,4-dioxane (5 mL) was heated with stirring in a sealed 10 mL of microwave process vial for 1 hour at 130° C. under microwave irradiation. The reaction mixture was concentrated in vacuo and the residue was purified by preparative HPLC to afford 20 mg of the desired product (yield was 5.3%).

Workup

  1. temperaturewas heated
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-de1e51e5bb244161b0f3d3b6a36059c3
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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