Citric Acid → Tert-butyl 3-((tert-butyldimethylsilyl)oxy)-5-(hydroxymethyl)piperidine-1-carboxylate

HRID 57534Notes

Reaction equation

HRID 57534 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12][CH:11]([C:22](OC)=[O:23])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li+].[BH4-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[Si:1]([O:8][CH:9]1[CH2:10][CH:11]([CH2:22][OH:23])[CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 4148881Lithium borohydrideHCID 711138811-(tert-Butyl) 3-methyl 5-((tert-butyldimethylsilyl)oxy)piperidine-1,3-dicarboxylate

Product 1

HCID 50896320Tert-butyl 3-((tert-butyldimethylsilyl)oxy)-5-(hydroxymethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-tert-butyl 3-methyl 5-(tert-butyldimethylsilyloxy)piperidine-1,3 from step A in THF (100 mL) was treated with LiBH4 (0.84 g, 38.5 mmol) at 0° C. stirring for 2 hours, warmed to room temperature, and then treated with citric acid (1M) till pH=4. The volatiles were removed in vacuo, and the residue was dissolved in ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound. MS (m/z): 246 (M-Boc+H)+.

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c9c5a2d15ef84d72bb081034cf6f33b1
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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