Potassium Carbonate → HCID 178455812, compound

HRID 1161644Notes

Reaction equation

HRID 1161644 reaction equation
[C:1]1(C)C=CC(S(N=[N+]=[N-])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].COP(CC(=O)C)(=O)OC.[C:30]([O:34][C:35](=[O:45])[NH:36][CH:37]1[CH2:42][CH2:41][CH:40]([CH:43]=O)[CH2:39][CH2:38]1)([CH3:33])([CH3:32])[CH3:31]>CC#N.CO>[C:30]([O:34][C:35](=[O:45])[NH:36][C@H:37]1[CH2:42][CH2:41][C@H:40]([C:43]#[CH:1])[CH2:39][CH2:38]1)([CH3:33])([CH3:32])[CH3:31]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 13661p-Toluenesulfonyl azideHCID 77872Dimethyl (2-oxopropyl)phosphonateHCID 11020615rac-tert-butyl N-[(1r,4r)-4-formylcyclohexyl]carbamate

Product 1

HCID 178455812HCID 178455812, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of p-toluenesulfonyl azide (10.57 g, 53.1 mmol) in MeCN (660 ml) were added K2CO3 (18.6 g, 134.5 mmol) and (2-oxo-propyl)-phosphonic acid dimethyl ester (7.3 ml, 53.1 mmol). The slurry was stirred at rt for 2 hours and a solution of (4-formyl-cyclohexyl)-carbamic acid tert-butyl ester (8.5 g, 37.4 mmol) in MeOH (100 ml) was added and the reaction proceeded overnight. The solvent was removed in vacuo. The residue was partitioned between water (100 ml) and EA (150 ml). The aq. layer was further extracted twice with EA (2×150 ml). The combined extracts were washed with brine and concentrated to dryness. The residue was chromatographed (Hex-EA 3-1) to afford the title alkyne (4.6 g, 55% yield) as a white solid.

Workup

  1. waitthe reaction proceeded overnight
  2. customThe solvent was removed in vacuo
  3. customThe residue was partitioned between water (100 ml) and EA (150 ml)
  4. extractionThe aq. layer was further extracted twice with EA (2×150 ml)
  5. washThe combined extracts were washed with brine
  6. concentrationconcentrated to dryness
  7. customThe residue was chromatographed (Hex-EA 3-1)

Sources & evidence

ORD record
ord-f6a0e64489a34981b30435582ccacb78
Source dataset
uspto-grants-2010_10
Patent number
US07820655B2

Reaction notes

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