p-Toluenesulfonic acid → HCID 86746067, compound

HRID 846704Notes

Reaction equation

HRID 846704 reaction equation
[CH2:1]([NH:8][C:9](=[O:11])[OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1.[Br:19][CH2:20][CH:21](O)[CH2:22][OH:23].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([NH:8][C:9](=[O:10])[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:19][CH2:20][CH:21]1[CH2:22][O:23][C:15]2([CH2:16][CH2:17][NH:12][CH2:13][CH2:14]2)[O:18]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 208273-Bromo-1,2-propanediolHCID 516892Sodium BicarbonateHCID 22440228HCID 22440228, compound

Product 1

HCID 86746067HCID 86746067, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A 5.00 g (21.43 mmol) sample of 4-piperidinone benzyl carbamate, from Step 2 Example 196, 4.69 mL (53.59 mmol) of 3-bromo-1,2-propanediol, and 0.200 g (1.07 mmol) of p-toluenesulfonic acid was added to 100 mL of toluene and the mixture was heated at 110° C. for 24 hours. The reaction solution was poured into 200 mL of 7% sodium bicarbonate solution, washed well, washed with water, dried over anhydrous sodium sulfate and the solvent removed under vacuum to afford 7.79 g of 2-bromomethyl-1,4-dioxa-8-azaspiro[4.5]decane benzyl carbamate, MS (DCl) M/Z 387 (M+NH4), 370 (M+H). NMR (CDCl3): d 1.69 (m, 4H), 3.31 (dd, 1H, J=9.0, 10.5 Hz), 3.44 (dd, 1H, J=6.0, 9.0 Hz), 3.58 (m, 4H), 3.90 (dd, 1H, J=6.0, 9.0 Hz), 4.14 (dd, 1H, J=6.0, 9.0 Hz), 4.37 (m, 1H), 5.13 (s, 2H), 7.34 (m, 5H).

Workup

  1. washwashed well
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-c3e3b099346a4c188023488c615f7a52
Source dataset
uspto-grants-1992_08
Patent number
US05137892

Reaction notes

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