Dichloromethane → HCID 67226684, compound

HRID 573171Notes

Reaction equation

HRID 573171 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-a2c79153e0f04579a67856638f9d7fbd
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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