Ammonia → Benzyl (4-carbamoylbicyclo[2.2.2]octan-1-yl)carbamate

HRID 227933Notes

Reaction equation

HRID 227933 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([OH:22])=O)([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:24]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.N>C(#N)C>[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([NH2:24])=[O:22])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 106622014-(Benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylic acid

Product 1

HCID 23150697Benzyl (4-carbamoylbicyclo[2.2.2]octan-1-yl)carbamateYield 89.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Benzyloxycarbonylaminobicyclo[2.2.2]octane-1-carboxylic acid (998 mg) was suspended in acetonitrile (20 mL). While the suspension was chilled in an ice bath, N-hydroxybenzotriazole (605 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (757 mg) were sequentially added. The mixture was stirred at room temperature for 4 hours and was left overnight. Subsequently, 25% aqueous ammonia (1.80 mL) was added while the reaction vessel was chilled in an ice bath. The mixture was then stirred at room temperature for 1 hour. The insoluble material was filtered and washed sequentially with acetonitrile and dichloromethane. The filtrate and the washings were combined and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluant:ethyl acetate) to give 4-benzyloxycarbonylaminobicyclo[2.2.2]octane-1-carboxamide (889 mg).

Workup

  1. temperatureWhile the suspension was chilled in an ice bath
  2. waitwas left overnight
  3. temperaturewas chilled in an ice bath
  4. stirringThe mixture was then stirred at room temperature for 1 hour
  5. filtrationThe insoluble material was filtered
  6. washwashed sequentially with acetonitrile and dichloromethane
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel chromatography (eluant:ethyl acetate)

Sources & evidence

ORD record
ord-ec25fb55fb3b45baa7db8d7d33612a69
Source dataset
uspto-grants-2009_07
Patent number
US07560569B2

Reaction notes

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