Water → HCID 58468062, compound

HRID 391188Notes

Reaction equation

HRID 391188 reaction equation
C[O:2][C:3]([C:5]1([CH2:11][CH2:12][CH2:13][NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=O.CC(C)([O-])C.[K+].O.[Sn]>C1COCC1.C(Cl)Cl.C(OCC)(=O)C.CO>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([N:14]2[CH2:13][CH2:12][CH2:11][C:5]3([CH2:10][CH2:9][O:8][CH2:7][CH2:6]3)[C:3]2=[O:2])=[CH:16][CH:17]=1

Participants

9

Reactant 4

HCID 962WaterHCID 5352426Tin atomHCID 23665647Potassium tert-butoxideHCID 58468047HCID 58468047, compound

Product 1

HCID 58468062HCID 58468062, compoundYield 94.9%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a clear solution of 4-[3-(4-Bromo-phenylamino)-propyl]-tetrahydro-pyran-4-carboxylic acid methyl ester (0.74 g, 2.08 mmol) in THF (25 mL) was added a solution of 1.0 mL of potassium t-butoxide (1M in THF) at r.t. (water bath at rt). The clear solution turned a little bit cloudy. After 15 min, TLC (5% MeOH in DCM) showed the reaction is complete (spot to spot), LC/MS detected the product peak. The reaction was cooled tin an ice-water bath, diluted with 25 mL of ethyl acetate, quenched with 10 mL of water. The two layers were separated. The aqueous layer was extracted with EtOAc (2×10 mL). The combined EtOAc extracts were washed with brine, and concentrated on rotavap to yield a crude product as a slightly yellow solid. This material was loaded onto a 25-g of silica gel column, eluted with DCM and 5% MeOH in DCM to get 0.64 g (86% yield) of the title compound as a white solid.

Workup

  1. customquenched with 10 mL of water
  2. customThe two layers were separated
  3. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  4. washThe combined EtOAc extracts were washed with brine
  5. concentrationconcentrated on rotavap
  6. customto yield a crude product as a slightly yellow solid
  7. washeluted with DCM and 5% MeOH in DCM

Sources & evidence

ORD record
ord-1d38de203d5546379e8b67efd551aa86
Source dataset
uspto-grants-2013_02
Patent number
US08383814B2

Reaction notes

Loading…