tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate → HCID 54775648, compound

HRID 1518972Notes

Reaction equation

HRID 1518972 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.CON(C)[C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)=[O:10]>O1CCCC1>[CH:1]1([C:9]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[O:10])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 11065582tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylateHCID 178418630HCID 178418630, compound

Product 1

HCID 54775648HCID 54775648, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add cyclopropylmagnesium bromide (4.8 g, 33.0 mmol) to a solution of tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (7.5 g, 27.5 mmol) in tetrahydrofuran (120 mL) at 0° C. Remove the cooling bath and stir at ambient temperature overnight. Add an additional cyclopropylmagnesium bromide (20 mL) and stir an additional 4 hours. Pour into a solution of saturated sodium bicarbonate and extract once with diethyl ether and once with EtOAc. Combine organic extracts, dry over sodium sulphate; filter; collect the filtrate; and concentrate under vacuum. Purify via flash column chromatography using a gradient of 0-40% ethyl acetate in hexane to give the title compound (6.4 g, 91.7%). MS (m/z): 198 (M+1-tBu).

Workup

  1. customRemove the cooling bath
  2. additionAdd an additional cyclopropylmagnesium bromide (20 mL)
  3. stirringstir an additional 4 hours
  4. additionPour into a solution of saturated sodium bicarbonate
  5. extractionextract once with diethyl ether and once with EtOAc
  6. dry with materialCombine organic extracts, dry over sodium sulphate
  7. filtrationfilter
  8. customcollect the filtrate
  9. concentrationand concentrate under vacuum
  10. customPurify via flash column chromatography

Sources & evidence

ORD record
ord-298162af0c5a42a2aceba32547798515
Source dataset
uspto-grants-2015_07
Patent number
US09073856B2

Reaction notes

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