Water → phenylmethyl (2S)-2-(hydroxymethyl)-1-piperidinecarboxylate

HRID 1366691Notes

Reaction equation

HRID 1366691 reaction equation
[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[C:17](O)=[O:18])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[OH:18][CH2:17][C@@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][N:11]1[C:9]([O:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 688345(S)-1-N-Cbz-Pipecolinic acid

Product 1

HCID 10879502phenylmethyl (2S)-2-(hydroxymethyl)-1-piperidinecarboxylateYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2S)-1-{[(Phenylmethyl)oxy]carbonyl}-2-piperidinecarboxylic acid (1.0 g, 3.798 mmol) in THF (5 mL) was cooled to −18° C. and borane-THF complex (3.798 mL, 3.798 mmol) was added over 10 min. The mixture was allowed to warm to room temperature with stirring overnight, then cooled to 0° C., and water (4 mL) was added, followed by K2CO3 (1.4 g). The phases were separated, and the aqueous phase was extracted with Et2O (3×25 mL). The combined organic phase was washed with brine (1×25 mL) and dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide phenylmethyl (2S)-2-(hydroxymethyl)-1-piperidinecarboxylate (815 mg, 86%). LCMS: (M+H)+: 250.2.

Workup

  1. additionborane-THF complex (3.798 mL, 3.798 mmol) was added over 10 min
  2. temperaturecooled to 0° C.
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with Et2O (3×25 mL)
  5. washThe combined organic phase was washed with brine (1×25 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-22782d7d14a94808999628919a1e049c
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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