Triethylsilane → N-(tert-Butoxycarbonyl)-D-prolinal

HRID 1670019Notes

Reaction equation

HRID 1670019 reaction equation
C(S[O:4][C:5](=O)[C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])C.C([SiH](CC)CC)C>CC(C)=O.[Pd]>[C:11]([N:7]1[CH2:8][CH2:9][CH2:10][C@@H:6]1[CH:5]=[O:4])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 86612822HCID 86612822, compound

Product 1

HCID 7009153N-(tert-Butoxycarbonyl)-D-prolinalYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 180AcetoneSolvent

Procedure

To a solution of (2R)-N-BOC-proline ethylthioester, prepared in Step A, in acetone were added dropwise triethylsilane (5.39 g, 46.3 mmol) and Pd/C (100 mg) at 0° C. When no further gas evolution occurred, the reaction mixture was warmed to rt and then stirred for additional 30 min. The reaction solution was filtered though Celite, the filtrate concentrated in vacuo. The residue was purified by column chomatography (EtOAc/Hex=1/2) to give the title compound (1.43 g, 93.2%).

Workup

  1. filtrationThe reaction solution was filtered though Celite
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified by column chomatography (EtOAc/Hex=1/2)

Sources & evidence

ORD record
ord-b9cc4f177c5e40ea8f28b2023f363937
Source dataset
uspto-grants-2011_08
Patent number
US07989634B2

Reaction notes

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