Dichloromethane → HCID 71247447, compound

HRID 1487002Notes

Reaction equation

HRID 1487002 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH:19]3[CH:24]4[CH:20]3[CH2:21][N:22](C(OC(C)(C)C)=O)[CH2:23]4)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(Cl)Cl.C([O-])(O)=O.[Na+]>>[CH:24]12[CH:19]([NH:18][C:16](=[O:17])[O:15][CH2:14][CH:12]3[C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[C:5]4[C:13]3=[CH:1][CH:2]=[CH:3][CH:4]=4)[CH:20]1[CH2:21][NH:22][CH2:23]2

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 71247928HCID 71247928, compound

Product 1

HCID 71247447HCID 71247447, compoundYield 69.1%

Procedure

tert-Butyl 6-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-azabicyclo[3.1.0]hexane-3-carboxylate (1.9 g, 1.0 eq.) was dissolved in DCM (20 mL) TFA (1.38 mL, 4 eq) was added dropwise at 0° C. and the reaction mixture was stirred at room temperature for 4 h. The reaction mixture was cooled to 0° C. and neutralized by saturated NaHCO3. The solid precipitated out was collected by filtration to afford 1.0 g of (9H-fluoren-9-yl)methyl 3-azabicyclo[3.1.0]hexan-6-ylcarbamate (69% yield).

Workup

  1. additionwas added dropwise at 0° C.
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customThe solid precipitated out
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-6b22d13f258c4129892e13954e953fab
Source dataset
uspto-grants-2016_08
Patent number
US09428490B2

Reaction notes

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