Cyclohexanone → HCID 67343263, compound

HRID 1669997Notes

Reaction equation

HRID 1669997 reaction equation
[C:1]([N:11]1[CH2:15][CH2:14][C@H:13]([NH2:16])[CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[C:17]1(=O)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[C:1]([N:11]1[CH2:15][CH2:14][C@H:13]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 1519355(S)-1-Cbz-3-AminopyrrolidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67343263HCID 67343263, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (3S)-1-Cbz-3-aminopyrrolidine (4.11 g, 16.0 mmol) and cyclohexanone (2.36 g, 24.0 mmol) in DCE (50 mL) was slowly added NaBH(OAc)3 (6.78 g, 32.0 mmol) at rt. The reaction mixture was quenched after 4 h using a saturated aqueous NaHCO3 solution and extracted with DCM followed by EtOAc. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc/Hex=2/1) to give the title compound (4.79 g, 98.1%).

Workup

  1. customat rt
  2. customThe reaction mixture was quenched after 4 h
  3. extractionextracted with DCM
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by flash chromatography (EtOAc/Hex=2/1)

Sources & evidence

ORD record
ord-604eb6d3055e48b4bf3e8a50446131a9
Source dataset
uspto-grants-2011_08
Patent number
US07989634B2

Reaction notes

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