Chlorotrimethylsilane → N-Boc-trans-4-hydroxy-L-prolinol

HRID 495052Notes

Reaction equation

HRID 495052 reaction equation
[Li+].[BH4-].C[Si](Cl)(C)C.[C:8]([O:12][C:13]([N:15]1[CH2:19][C@H:18]([OH:20])[CH2:17][C@H:16]1[C:21](O)=[O:22])=[O:14])([CH3:11])([CH3:10])[CH3:9]>C1COCC1>[OH:20][C@H:18]1[CH2:19][N:15]([C:13]([O:12][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:14])[C@H:16]([CH2:21][OH:22])[CH2:17]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acidHCID 4148881Lithium borohydride

Product 1

HCID 11275979N-Boc-trans-4-hydroxy-L-prolinolYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. suspension of LiBH4 (2.0 equiv) in THF (0.67 M) was slowly added TMSCl (4.0 equiv) by syringe. After stirring at room temperature for 30 minutes, (2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (1.0 equiv) was then added, and the resulting mixture was stirred at room temperature overnight. The reaction was quenched by the careful addition of sat'd. aq. NaHCO3, and the mixture was diluted with EtOAc, and the organice layer was washed twice with sat'd. aq. NaHCO3, once with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The title compound was isolated in 65% yield and used without further purification.

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe reaction was quenched by the careful addition of sat'd
  3. additionaq. NaHCO3, and the mixture was diluted with EtOAc
  4. washthe organice layer was washed twice with sat'd
  5. dry with materialaq. NaHCO3, once with brine, dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-50c252175caf44488509e6d1976c63f6
Source dataset
uspto-grants-2009_05
Patent number
US07538223B2

Reaction notes

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