Sodium Chloride → HCID 89585232, compound

HRID 714765Notes

Reaction equation

HRID 714765 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([C@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]1)=[O:7].[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].[Cl-].[Na+].C(OCC)(=O)C>O1CCCC1>[OH:7][CH:6]([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)[C@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[CH2:9]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 895852361-Piperidinecarboxylic acid, 3-(2-thiazolylcarbonyl)-, 1,1-dimethylethyl ester, (3S)-

Product 1

HCID 89585232HCID 89585232, compoundYield 109.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, 17.2 g (0.058 mol) of tert-butyl (S)-3-(thiazole-2-carbonyl)-piperidine-1-carboxylate were dissolved in 200 ml of tetrahydrofuran, and 121.8 ml (0.122 mol) of lithium tri-tert-butoxyaluminium hydride (1.0 M solution in tetrahydrofuran) were subsequently added dropwise between −4 and +2° C. The reaction mixture was stirred at 0° C. for 30 minutes and then at room temperature for 1 hour. Ice-water was subsequently added, during which the temperature rose to 1° C. After addition of saturated sodium chloride solution and ethyl acetate, the inorganic residue was filtered off. Water and saturated sodium chloride solution were added to the filtrate, which was then extracted with ethyl acetate, and the organic phase was evaporated, giving 19.0 g of tert-butyl (S)-3-(hydroxythiazol-2-ylmethyl)piperidine-1-carboxylate as diastereomer mixture of the S-piperidine in the ratio 30:70 (polar:nonpolar); HPLC/MS (M+H)+=299; rotation value in methanol [α]20D=+4.80. 1H NMR (400 MHz, DMSO) δ 7.72 (dd, J=14.9, 3.3, 1H), 7.62 (dd, J=3.2, 0.8, 1H), 6.22 (dd, J=11.4, 5.3, 1H), 4.66 (dd, J=9.8, 4.6, 1H), 3.82 (t, J=11.8, 2H), 2.71-2.54 (m, 2H), 1.88-1.72 (m, 1H), 1.73-1.57 (m, 2H), 1.40-1.30 (m, 11H).

Workup

  1. waitat room temperature for 1 hour
  2. customrose to 1° C
  3. filtrationthe inorganic residue was filtered off
  4. additionWater and saturated sodium chloride solution were added to the filtrate, which
  5. extractionwas then extracted with ethyl acetate
  6. customthe organic phase was evaporated

Sources & evidence

ORD record
ord-f0f17aecbbc040ab9eb6ef3fe612c03f
Source dataset
uspto-grants-2015_11
Patent number
US09187469B2

Reaction notes

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