Cyclopentanone → HCID 86692133, compound

HRID 527894Notes

Reaction equation

HRID 527894 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])(C)C)=[O:8])[CH2:3]1.[C:14]1(=O)[CH2:18][CH2:17][CH2:16][CH2:15]1.[BH-](OC(C)=O)(OC(C)=O)O[C:22]([CH3:24])=O.[Na+]>C1COCC1>[CH:14]1([NH:1][C@@H:2]2[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][CH2:13][CH2:22][CH3:24])=[O:8])[CH2:3]2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 8452CyclopentanoneHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 86692133HCID 86692133, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-tert-butyl 3-aminopyrrolidine-1-carboxylate (1.0 g, 5.3 mmol) and cyclopentanone (451 mg, 5.3 mmol) in THF (20 mL) was slowly added NaBH(OAc)3 (1.13 g, 5.3 mmol) and then stirred at the ambient temperature for overnight. The reaction was quenched with H2O (20 mL) and extracted with dichloromethane (3×20 mL). The combined extracts were washed with brine (3×5 mL), dried over anhydrous Na2SO4, filtered and concentrated to give the title compound. MS (m/z): 255 (M+H)+.

Workup

  1. customThe reaction was quenched with H2O (20 mL)
  2. extractionextracted with dichloromethane (3×20 mL)
  3. washThe combined extracts were washed with brine (3×5 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a150873d8c32497b9ba8a3b3a63181a4
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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