(R)-3-Pyrrolidinol → HCID 59551744, compound

HRID 1170239Notes

Reaction equation

HRID 1170239 reaction equation
[CH3:1][C:2]([O-:5])(C)C.[K+].[CH2:7]1[C@@H:11]([OH:12])[CH2:10][NH:9][CH2:8]1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([C:26]2[C:35]3[C:30](=[CH:31][C:32](F)=[CH:33][CH:34]=3)[N:29]=[CH:28][N:27]=2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>C1COCC1>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([C:26]2[C:35]3[C:30](=[CH:31][C:32]([O:12][C@@H:11]4[CH2:7][CH2:8][N:9]([C:2](=[O:5])[CH3:1])[CH2:10]4)=[CH:33][CH:34]=3)[N:29]=[CH:28][N:27]=2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 2759337(R)-3-PyrrolidinolHCID 23665647Potassium tert-butoxideHCID 595517364-(7-Fluoro-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59551744HCID 59551744, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of KOt-Bu (55.1 mg, 0.47 mmol) in THF (1 mL) was added (R)-hydroxypyrrolidine (37.7 mg, 0.43 mmol), followed by 4-(7-fluoro-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester (110.3 mg, 0.33 mmol), which was prepared as described in Example 12b, in THF (1 mL). The mixture was stirred for 1 h at room temperature, quenched with (CH3CO)2O. The mixture was then partitioned between EtOAc and water. The organic extracts were washed with brine and evaporated and the residue was used for the next step reaction without further purification. LC/MS for C24H33N4O4 (MH+) 440.2, found 440.5.

Workup

  1. customwas prepared
  2. customquenched with (CH3CO)2O
  3. customThe mixture was then partitioned between EtOAc and water
  4. washThe organic extracts were washed with brine
  5. customevaporated
  6. customthe residue was used for the next step reaction without further purification

Sources & evidence

ORD record
ord-70fcb7a408364f6a90ad3db5e7239ff3
Source dataset
uspto-grants-2010_11
Patent number
US07825244B2

Reaction notes

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