1-Octanethiol → 2,5-Diazabicyclo[4.1.0]heptane-2-carboxylic Acid DiMethylethyl Ester

HRID 2173432Notes

Reaction equation

HRID 2173432 reaction equation
[CH:1]12[CH2:7][CH:6]1[N:5](C(OCC1C3C=CC=CC=3C3C1=CC=CC=3)=O)[CH2:4][CH2:3][N:2]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].C(S)CCCCCCC.C1CCN2C(=NCCC2)CC1>CCOCC>[CH:1]12[CH2:7][CH:6]1[NH:5][CH2:4][CH2:3][N:2]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]

Participants

5

Reactant 3

HCID 81441-OctanethiolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1015019572-(1,1-Dimethylethyl) 5-(9H-fluoren-9-ylmethyl) 2,5-diazabicyclo[4.1.0]heptane-2,5-dicarboxylate

Product 1

HCID 509864522,5-Diazabicyclo[4.1.0]heptane-2-carboxylic Acid DiMethylethyl Ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

tert-Butyl (±)-9H-fluoren-9-ylmethyl 2,5-diazabicyclo[4.1.0]heptane-2,5-dicarboxylate (1.05 g, 2.50 mmol) was dissolved in Ether (25 mL) and was treated with 1-octanethiol (3.65 g, 24.97 mmol) at room temperature for 10 minutes. Then DBU (0.151 mL, 0.999 mmol) was added. Let mixture stir for 4 hours. Then solvent and extra 1-Octanethiol was removed under reduced pressure. And residue was put on 40 gram silica gel column and eluted on ISCO (0-15% MeOH/EtOAc). Removing solvent gave the title compound. 1H NMR (ppm) (500 MHz, CDCl3): δ 3.51-3.45 (1H, m), 3.05-2.58 (5H, m), 1.71 (1H, s), 1.45 (9H, s), 0.88-0.77 (1H, m), 0.53-0.44 (1H, m).

Workup

  1. customThen solvent and extra 1-Octanethiol was removed under reduced pressure
  2. washeluted on ISCO (0-15% MeOH/EtOAc)

Sources & evidence

ORD record
ord-a554ecaf880d40329a23f5ac2513d6f5
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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