Water → 2-(4-Bromo-2-methyl-phenyl)-8-oxa-2-aza-spiro[4.5]decan-1-one

HRID 391183Notes

Reaction equation

HRID 391183 reaction equation
C[O:2][C:3]([C:5]1([CH2:11][CH2:12][NH:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:15]=2[CH3:21])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=O.CC(C)([O-])C.[K+].O.[Sn]>C1COCC1.C(Cl)Cl.CO>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([N:13]2[CH2:12][CH2:11][C:5]3([CH2:10][CH2:9][O:8][CH2:7][CH2:6]3)[C:3]2=[O:2])=[C:15]([CH3:21])[CH:16]=1

Participants

8

Reactant 4

HCID 962WaterHCID 5352426Tin atomHCID 23665647Potassium tert-butoxideHCID 674223094-[2-(4-Bromo-2-methyl-phenylamino)-ethyl]-tetrahydro-pyran-4-carboxylic acid methyl ester

Product 1

HCID 584680462-(4-Bromo-2-methyl-phenyl)-8-oxa-2-aza-spiro[4.5]decan-1-oneYield 98.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a clear solution of 4-[2-(4-Bromo-2-methyl-phenylamino)-ethyl]-tetrahydro-pyran-4-carboxylic acid methyl ester (2 g, 5.6 mmol) in THF (80 mL) was added a solution of potassium t-butoxide (1M in THF) 2.5 mL (2.5 mmol, 0.45 equiv.) at r.t. (water bath at rt). The clear solution turned a little bit cloudy. After 30 min, TLC (5% MeOH in DCM) showed the reaction is complete (spot to spot), LC/MS detected the product peak of 324/326 (t 3.267 min). The reaction was cooled tin an ice-water bath, diluted with 100 mL of DCM, quenched with 20 mL of water. The two layers were separated. The aqueous layer was extracted with DCM (2×20 mL). The combined DCM extracts were washed with brine, and concentrated on rotavap to yield 1.79 g (98% yield) of the title product as a white solid.

Workup

  1. customthe product peak of 324/326 (t 3.267 min)
  2. customquenched with 20 mL of water
  3. customThe two layers were separated
  4. extractionThe aqueous layer was extracted with DCM (2×20 mL)
  5. washThe combined DCM extracts were washed with brine
  6. concentrationconcentrated on rotavap

Sources & evidence

ORD record
ord-d335ac0603ca4528abdd1379c6f14ab7
Source dataset
uspto-grants-2013_02
Patent number
US08383814B2

Reaction notes

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