Tetrabutylammonium Fluoride → (S)-tert-butyl 1-hydroxy-3-(2-oxopiperidin-1-yl)propan-2-ylcarbamate

HRID 451817Notes

Reaction equation

HRID 451817 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=[O:18])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CC#N>[OH:8][CH2:9][C@@H:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=[O:18]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59201533(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-(2-oxopiperidin-1-yl)propan-2-ylcarbamate

Product 1

HCID 59201613(S)-tert-butyl 1-hydroxy-3-(2-oxopiperidin-1-yl)propan-2-ylcarbamateYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

To a suspension of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-(2-oxopiperidin-1-yl)propan-2-ylcarbamate (370 mg, 0.96 mmol) in CH3CN (3 mL) was added TBAF (750 mg, 2.88 mmol). The reaction mixture was stirred for 1 h at 50-60° C. The reaction mixture was concentrated in vacuo and then EA was added. This solution was washed with brine, water and concentrated again to afford crude (S)-tert-butyl 1-hydroxy-3-(2-oxopiperidin-1-yl)propan-2-ylcarbamate (260 mg 100%), which was used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionEA was added
  3. washThis solution was washed with brine, water
  4. concentrationconcentrated again

Sources & evidence

ORD record
ord-dddfa08975dd4e048022240d728e4126
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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