Triethylamine → HCID 66744383, compound

HRID 1959437Notes

Reaction equation

HRID 1959437 reaction equation
C(N(CC)CC)C.[CH2:8]([S:10](Cl)(=[O:12])=[O:11])[CH3:9].[CH:14]12[NH:21][CH:18]([CH2:19][CH2:20]1)[CH2:17][N:16]([C:22]([O:24][CH2:25][CH:26]1[C:38]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:32]3[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:23])[CH2:15]2>>[CH2:8]([S:10]([N:21]1[CH:18]2[CH2:19][CH2:20][CH:14]1[CH2:15][N:16]([C:22]([O:24][CH2:25][CH:26]1[C:38]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:32]3[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:23])[CH2:17]2)(=[O:12])=[O:11])[CH3:9]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 66745343HCID 66745343, compound2×

Product 1

HCID 66744383HCID 66744383, compound

Procedure

To the solution of (9H-fluoren-9-yl)methyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate in DCM (2 mL) from step 2 was added triethylamine (100 mg, 138 μL, 1.0 mmol) and ethanesulfonyl chloride (190 mg, 140 μL, 1.4 mmol). The reaction mixture was stirred for 16 h. The reaction mixture was washed with 50% saturated bicarbonate solution and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to obtain (9H-fluoren-9-yl)methyl 8-(ethylsulfonyl)-3,8-diazabicyclo[3.2.1]octane-3-carboxylate, which was used directly for the next step. LC/MS m/z 427.5 [M+H]+.

Workup

  1. washThe reaction mixture was washed with 50% saturated bicarbonate solution and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d563d893d7c44026bb5b923d5575bc56
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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