1,4-Dibromobutane → (4-Pyrrolidin-1-yl-cyclohexylmethyl)-carbamic acid benzyl ester

HRID 1819479Notes

Reaction equation

HRID 1819479 reaction equation
[CH2:1]([O:8][C:9](=[O:19])[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH:15]([NH2:18])[CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:27][CH2:28][CH2:29][CH2:30]Br>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:8][C:9](=[O:19])[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH:15]([N:18]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:14][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 59845659Benzyl [(cis-4-aminocyclohexyl)methyl]carbamate

Product 1

HCID 69058995(4-Pyrrolidin-1-yl-cyclohexylmethyl)-carbamic acid benzyl esterYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4-amino-cyclohexylmethyl)-carbamic acid benzyl ester (350 mg, 1.34 mmol) in DMF (5 mL) was added K2CO3 (924 mg, 6.70 mmol) and 1,4-dibromobutane (160 mL, 1.34 mmol). The reaction mixture was stirred at room temperature for 14 h before diluting with EtOAc (100 mL). The reaction solution was washed with water (2×100 mL) and brine before concentrating in vacuo. The residue was purified by chromatography using a 12 g ISCO combi-flash cartridge (silica gel, 95:4.75:0.25 DCM/MeOH/NH4OH) to afford (4-pyrrolidin-1-yl-cyclohexylmethyl)-carbamic acid benzyl ester (351 mg, 83%) as an off-white solid.

Workup

  1. washThe reaction solution was washed with water (2×100 mL) and brine
  2. concentrationbefore concentrating in vacuo
  3. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-e95d56347059468489654d1791d1a7b3
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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