Sodium triacetoxyborohydride → HCID 86698025, compound

HRID 518871Notes

Reaction equation

HRID 518871 reaction equation
[O:1]1[CH2:4][C:3](=O)[CH2:2]1.[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][CH2:18][C@@H:17]([NH2:21])[CH2:16]2)=[CH:11][C:10]=1[O:22][CH:23]([CH3:25])[CH3:24])([O-:8])=[O:7].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(=O)([O-])O.[Na+]>[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][CH2:18][C@@H:17]([NH:21][CH:3]3[CH2:2][O:1][CH2:4]3)[CH2:16]2)=[CH:11][C:10]=1[O:22][CH:23]([CH3:25])[CH3:24])([O-:8])=[O:7]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 86698023HCID 86698023, compound

Product 1

HCID 86698025HCID 86698025, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
70 °C

Procedure

2 ml of 3-oxetanone are added, at a temperature of about 20° C., to a solution of 1.50 g of (3R)-1-[4-nitro-3-(propan-2-yloxy)phenyl]piperidin-3-amine in 54 ml of 1,4-dichloroethane, under an argon atmosphere. After stirring of the mixture, 3.69 g of sodium triacetoxyborohydride are added in small portions and the reaction mixture is heated at 70° C. for 3 h. After returning to ambient temperature, 70 ml of a dilute sodium hydrogen carbonate solution are added. The aqueous phase is extracted twice with 80 ml of dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered and concentrated under vacuum, so as to obtain an orangey-coloured oily residue. The residue is purified by chromatography on silica gel, using a dichloromethane/isopropanol (98/2 to 94/6) elution gradient, so as to obtain 1.2 g of (3R)-1-[4-nitro-3-(propan-2-yloxy)phenyl]-N-(oxetan-3-yl)piperidin-3-amine in the form of an orangey-coloured gum.

Workup

  1. additionare added in small portions
  2. customAfter returning to ambient temperature
  3. extractionThe aqueous phase is extracted twice with 80 ml of dichloromethane
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customso as to obtain an orangey-coloured oily residue
  8. customThe residue is purified by chromatography on silica gel
  9. washa dichloromethane/isopropanol (98/2 to 94/6) elution gradient

Sources & evidence

ORD record
ord-ed22a63445234ddb95f1efd544aa1917
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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