Dichloromethane → HCID 67226684, compound

HRID 624447Notes

Reaction equation

HRID 624447 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([NH:7]C(=O)OC(C)(C)C)[CH2:2]1.[F:15][CH2:16][C:17](=O)[CH2:18][F:19].[Na].[Cl:22]CCl>>[ClH:22].[F:15][CH2:16][CH:17]([N:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([NH2:7])[CH2:2]1)[CH2:18][F:19]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 2283971,3-DifluoroacetoneHCID 1514172(3R)-3-Aminopiperidine, 3-BOC protectedHCID 5360545Sodium

Product 1

HCID 67226684HCID 67226684, compound

Procedure

A solution of (R)-tert-butyl piperidin-3-ylcarbamate (0.500 g), 1,3-difluoropropan-2-one (0.258 g) and sodium triacetoxyhydroborate (0.794 g) were stirred together in dichloromethane (5 mL) overnight. The reaction was quenched with saturated aqueous NaHCO3 (10 mL) and extracted with dichloromethane (30 mL). The organic layer was washed with brine (20 mL), dried over magnesium sulfate, filtered, and concentrated. The crude material was treated with HCl (4.0M dioxane, 2 mL) in methanol (2 mL). After stirring for 2 hours, the reaction was concentrated to provide the title compound.

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3 (10 mL)
  2. extractionextracted with dichloromethane (30 mL)
  3. washThe organic layer was washed with brine (20 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionThe crude material was treated with HCl (4.0M dioxane, 2 mL) in methanol (2 mL)
  8. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-8d2255ab3147401b91c17863c3222d98
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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