Acetic Acid → HCID 86724503, compound

HRID 81150Notes

Reaction equation

HRID 81150 reaction equation
[CH2:1]([N:8]1[CH:13]2[CH:9]1[CH2:10][CH2:11][C:12]2([F:15])[F:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([OH:19])(=[O:18])[CH3:17]>CC#N>[C:16]([O:19][C@@H:9]1[CH2:10][CH2:11][C:12]([F:15])([F:14])[C@H:13]1[NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 867245046-Benzyl-2,2-difluoro-6-azabicyclo[3.1.0]hexane

Product 1

HCID 86724503HCID 86724503, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 6-benzyl-2,2-difluoro-6-azabicyclo[3.1.0]hexane (25 mg, 0.11 mmol) in CH3CN (1 mL), acetic acid (1 mL) was added at room temperature. The reaction mixture was heated to 80° C. for 16 h, cooled to room temperature and concentrated in vacuo. Purification of the residue on a silica gel column with 0 to 20% EtOAc/Hexanes afforded trans-2-(benzylamino)-3,3-difluorocyclopentyl acetate. MS ESI calc'd. for C14H17F2NO2 [M+H]+ 270. found 270.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customPurification of the residue on a silica gel column with 0 to 20% EtOAc/Hexanes

Sources & evidence

ORD record
ord-3bf56ea3f28a4051af3025a764406e14
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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