Methanesulfonyl chloride → 1,1-Dimethylethyl hexahydro-4-(methylsulfonyl)-1H-1,4-diazepine-1-carboxylate

HRID 2403396Notes

Reaction equation

HRID 2403396 reaction equation
[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(N(CC)CC)C>[C:4]([O:3][C:1]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([S:16]([CH3:15])(=[O:18])=[O:17])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 220612771,1-Dimethylethyl hexahydro-4-(methylsulfonyl)-1H-1,4-diazepine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 1-BOC-homopiperazine (0.8 ml) was added methane sulphonyl chloride (0.34 ml) and triethylamine (0.68 ml). The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was then partitioned between dichloromethane and water. The combined organic extracts were then washed with brine and dried (MgSO4). The solvent was removed in vacuo to yield 1.23 g crude 4-methanesulfonyl-[1,4]diazepane-1-carboxylic acid tert-butyl ester.

Workup

  1. customThe reaction mixture was then partitioned between dichloromethane and water
  2. washThe combined organic extracts were then washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a42c2077cf93487ab2c009e93e33de89
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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