Sodium borohydride → HCID 69559203, compound

HRID 2213039Notes

Reaction equation

HRID 2213039 reaction equation
[CH2:1]([C:5]1([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)[CH2:2][CH:3]=C.[BH4-].[Na+].ClCCl.C[OH:34]>>[OH:34][CH2:3][CH2:2][CH2:1][C:5]1([C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:7][CH2:6]1

Participants

4

Reactant 3

HCID 4311764Sodium borohydrideHCID 21226129Dichloromethane methanolHCID 53446371HCID 53446371, compound

Product 1

HCID 69559203HCID 69559203, compoundYield 99%

Procedure

A solution of 1-(1,1-dimethylethyl) 4-phenylmethyl 4-(3-butenyl)-1,4-piperidinedicarboxylate (Description 135, 1.06 g, 2.84 mmol) in dichloromethane/methanol (50:50, 20 mL) was cooled to −78° C. and oxygen was bubbled through the mixture for 10 minutes. Ozone was bubbled through the mixture until a blue coloration persisted. Oxygen was bubbled through the mixture for 10 minutes, then nitrogen for 10 minutes. Sodium borohydride (1.1 g, 28.9 mmol) was added over 5 minutes and the mixture was allowed to warm to room temperature. The solvent was evaporated under reduced pressure and water (40 mL) was added. The mixture was extracted with ethyl acetate (3×40 mL), the combined organic fractions were dried (Na2SO4) and the solvent was evaporated under reduced pressure to give the title compound (1.06 g, 99%). 1H NMR (400 MHz, CDCl3) δ 7.4–7.3 (5H, m), 5.15 (2H, s), 3.95–3.75 (2H, m), 3.52 (2H, t, J 7 Hz), 2.95–2.80 (2H, m), 2.12 (2H, br d, J 10 Hz), 1.65–1.30 (7H, m), and 1.44 (9H, s).

Workup

  1. customoxygen was bubbled through the mixture for 10 minutes
  2. customOzone was bubbled through the mixture until a blue coloration
  3. customOxygen was bubbled through the mixture for 10 minutes
  4. customThe solvent was evaporated under reduced pressure and water (40 mL)
  5. additionwas added
  6. extractionThe mixture was extracted with ethyl acetate (3×40 mL)
  7. dry with materialthe combined organic fractions were dried (Na2SO4)
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-17c494f2d8194592ab1c955d91a088bc
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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