(R)-3-Pyrrolidinol → HCID 68695646, compound

HRID 657268Notes

Reaction equation

HRID 657268 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][CH: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 68695646HCID 68695646, 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 65b, 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-692e8068b66242ac91046183c17c5087
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

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