Carbon Dioxide → 5-Methoxy-1-phenyl-1-(pyrrolidin-3-yl)pentan-1-ol

HRID 253553Notes

Reaction equation

HRID 253553 reaction equation
[OH:1][C:2]([CH:15]1[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH3:8].Cl.C([O-])([O-])=O.[K+].[K+].C(=O)=O>CC#N>[CH3:8][O:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH:15]1[CH2:19][CH2:18][NH:17][CH2:16]1)[OH:1]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 57786486Tert-butyl 3-(1-hydroxy-5-methoxy-1-phenylpentyl)pyrrolidine-1-carboxylate

Product 1

HCID 574196125-Methoxy-1-phenyl-1-(pyrrolidin-3-yl)pentan-1-olYield 66.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of tert-butyl 3-(1-hydroxy-5-methoxy-1-phenylpentyl)pyrrolidine-1-carboxylate (290 mg, 0.80 mmol) in MeCN (20 mL) was added 5% aq HCl (20 mL). The mixture was stirred at rt for 17 h and solid K2CO3 was added until CO2 evolution ceased. MeCN was removed under reduced pressure and the aqueous residue was extracted with CH2Cl2 (2×90 mL). The combined organic extracts were dried over Na2SO4 and concentrated to afford 5-methoxy-1-phenyl-1-(pyrrolidin-3-yl)pentan-1-ol (140 mg, 66%) as an oil.

Workup

  1. customMeCN was removed under reduced pressure
  2. extractionthe aqueous residue was extracted with CH2Cl2 (2×90 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c2be04b13f34448bb8fa48466ed67ce2
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

Loading…