Triethylamine → HCID 66744271, compound

HRID 1959435Notes

Reaction equation

HRID 1959435 reaction equation
[CH:1]12[N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:5]([CH2:6][CH2:7]1)[CH2:4][NH:3][CH2:2]2.C(N(CC)CC)C.[C:23](Cl)(=[O:39])[O:24][CH2:25][CH:26]1[C:38]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[C:32]2[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=2>ClCCl>[CH:1]12[N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:23]([O:24][CH2:25][CH:26]1[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=3[C:33]3[C:38]1=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:39])[CH2:2]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 343679-Fluorenylmethyl chloroformateHCID 157409088-Boc-3,8-diaza-bicyclo(3.2.1)octane

Product 1

HCID 66744271HCID 66744271, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 3,8-diazabicyclo[3.2.1]octane-8-carboxylate (105 mg, 0.5 mmol) in dichloromethane (3 mL) and triethylamine (100 mg, 138 μL, 1.0 mmol) was treated with 9H-fluoren-9-ylmethyl carbonochloridate (128.0 mg, 0.5 mmol). The reaction mixture was stirred for 1 h. The reaction mixture was washed with 1 N HCl, water, 50% saturated bicarbonate and brine. The organic layer was dried over Na2SO4, filtered and concentrated to obtain a solution of 3-(9H-fluoren-9-yl)methyl 8-tert-butyl 3,8-diazabicyclo[3.2.1]octane-3,8-dicarboxylate in DCM (2 mL), which was used directly for the next step. LC/MS m/z 435.5 [M+H]+.

Workup

  1. washThe reaction mixture was washed with 1 N HCl, water, 50% saturated bicarbonate and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8c20cc8662e24b65a558aacf07b41926
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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