Water → (S)-1-N-Cbz-Pipecolinic acid

HRID 1157137Notes

Reaction equation

HRID 1157137 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][N:6]1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:4].O.[OH-].[Li+]>C1COCC1>[CH2:14]([O:13][C:11]([N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C@H:5]1[C:3]([OH:4])=[O:2])=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium Hydroxide2×HCID 45072536S-Methyl 1-cbz-piperidine-2-carboxylate

Product 1

HCID 688345(S)-1-N-Cbz-Pipecolinic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of (S)-1-(benzyloxy-carbonyl)-2-piperidinecarboxylic acid methyl ester (2.00 g, 7.21 mmol) in THF (20 ml) at room temperature was treated with water (10 ml). Lithium hydroxide (190 mg, 7.93 mmol) was added and the resulting mixture stirred at room temperature for 3 hr. An additional quantity of lithium hydroxide (40 mg, 1.67 mmol) was added and the resulting mixture was stirred for 2 hr prior to the removal of the organic solvent. The resulting solution was washed with diethyl ether and the remaining aqueous layer was made acidic with 2 N HCl prior to a second extraction step with ethyl acetate. The organic layer was then recovered, dried (Na2SO4), filtered and concentrated to reveal a colorless oil (1.9927 g, 105%) which crystallized upon standing: 1H NMR (400 MHz, CDCl3) δ 1.30-1.88 (5H, m), 2.22-2.41 (1H, m), 3.00-3.21 (1H, m), 4.08-4.25 (1H, m), 4.91-5.30 (3H, m), 7.27-7.48 (5H, m).

Workup

  1. stirringthe resulting mixture was stirred for 2 hr
  2. customto the removal of the organic solvent
  3. washThe resulting solution was washed with diethyl ether
  4. extractionto a second extraction step with ethyl acetate
  5. customThe organic layer was then recovered
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customcrystallized

Sources & evidence

ORD record
ord-77957d26de144dfba7b2f93bb2824e5b
Source dataset
uspto-grants-2010_10
Patent number
US07807659B2

Reaction notes

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