Tetrahydrofuran → tert-Butyl 4-azido-3-hydroxypiperidine-1-carboxylate

HRID 1593451Notes

Reaction equation

HRID 1593451 reaction equation
[N:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][C:5]1=[O:17])=[N+:2]=[N-:3].C1COCC1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[NH4+].[Cl-]>O>[N:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:6][CH:5]1[OH:17])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 3611392Lithium tri-s-butylborohydrideHCID 21874153(+/-)-Tert-butyl 4-azido-3-oxopiperidine-1-carboxylate

Product 1

HCID 21874176tert-Butyl 4-azido-3-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of Compound 201A prepared above in dry THF (2 mL) cooled at −78° C. was added L-Selectride (1.0 M in THF, 0.98 mL, 0.98 mmol). The mixture was stirred at −78° C. for 2.0 hrs. Saturated NH4Cl (2 mL) was added and the reaction mixture was allowed to warm to room temperature. The mixture was diluted with water and extracted with EtOAc (3×). The combined organic layers were washed once with brine and dried over anhydrous Na2SO4. Concentration in vacuo followed by flash chromatography (hexane-EtOAc 4:1) on silica gel gave 44 mg of Compound 201B as an oil. 1H-NMR (400 mHz, CDCl3): 3.84 (m, 1H), 3.69 (m, 1H), 3.58 (m, 2H), 3.40 (m, 1H), 3.30 (m, 1H), 1.96 (m, 1H), 1.73 (m, 1H), 1.46 (s, 9H).

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed once with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-dfa9b86a2fd54d92b13bbfab860e3801
Source dataset
uspto-grants-2007_11
Patent number
US07297695B2

Reaction notes

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