tert-butyl N-(pyrrolidin-3-yl)carbamate → HCID 86689057, compound

HRID 75139Notes

Reaction equation

HRID 75139 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)=[CH:4][C:3]=1[NH:15][C@@H:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])[CH3:17].[C:26]([O:30][C:31]([NH:33][CH:34]1[CH2:38][CH2:37][NH:36][CH2:35]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:36]3[CH2:37][CH2:38][CH:34]([NH:33][C:31](=[O:32])[O:30][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:35]3)[CH2:10][CH2:9]2)=[CH:4][C:3]=1[NH:15][C@@H:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])[CH3:17]

Participants

5

Reactant 3

HCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 86689058HCID 86689058, compound

Product 1

HCID 86689057HCID 86689057, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of (R)-1-(4-chloro-3-(1-(2,4-dichlorophenyl)ethylamino)phenyl)piperidin-4-one (0.13 g, 0.32 mmol) and 3-(t-butoxycarbonylamino)pyrrolidine (0.24 g, 1.3 mmol) in dichloroethane (DCE) (2 mL) was added NaBH(OAc)3 (0.094 g, 0.44 mmol). The reaction mixture was heated at 80° C. for 4 h. The reaction mixture was quenched with aqueous saturated sodium bicarbonate and extracted with dichloromethane. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The resulting crude was purified by flash chromatography (SiO2, 1-7% methanol in dichloromethane) to give t-butyl 1-(1-(4-chloro-3-((R)-1-(2,4-dichlorophenyl)ethylamino)phenyl)piperidin-4-yl)pyrrolidin-3-ylcarbamate (0.092 g, 0.16 mmol, 31%).

Workup

  1. customThe reaction mixture was quenched with aqueous saturated sodium bicarbonate
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude was purified by flash chromatography (SiO2, 1-7% methanol in dichloromethane)

Sources & evidence

ORD record
ord-3a4c06415dc141caa169ef35d842b054
Source dataset
uspto-grants-2014_09
Patent number
US08835419B2

Reaction notes

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