Sodium hydride → (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-(2-oxopiperidin-1-yl)propan-2-ylcarbamate

HRID 451816Notes

Reaction equation

HRID 451816 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:11][NH:12][C:13](=[O:19])[CH2:14][CH2:15][CH2:16][CH2:17]Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+]>CN(C=O)C.CCOC(C)=O>[Si:1]([O:8][CH2:9][C@@H:10]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=[O:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 59201711(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-(5-chloropentanamido)propan-2-ylcarbamate

Product 1

HCID 59201533(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-(2-oxopiperidin-1-yl)propan-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Upon cooling a solution of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-(5-chloropentanamido)propan-2-ylcarbamate (500 mg, 1.18 mmol) in DMF (10 mL) to 0° C., NaH (52 mg, 1.30 mmol) was added. The reaction mixture was stirred for 4 h. The mixture was taken up in EtOAc, washed with saturated NaCl solution, dried over Na2SO4, concentrated under reduced pressure and the crude (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-(2-oxopiperidin-1-yl)propan-2-ylcarbamate was used in next step without purification (370 mg, 81%). 1H NMR (CDCl3, 300 MHz) δ 5.25 (d, 1H), 4.04-3.81 (m, 2H), 3.67-3.20 (m, 4H), 2.36 (m, 2H), 1.78 (m, 4H), 1.41 (s, 9H), 0.88 (s, 9H), 0.0 (s, 6H).

Workup

  1. washwashed with saturated NaCl solution
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customthe crude (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-(2-oxopiperidin-1-yl)propan-2-ylcarbamate was used in next step without purification (370 mg, 81%)

Sources & evidence

ORD record
ord-1d728bd8103a4dc3837adc257d403aca
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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