Isopropylamine → Tert-butyl 3-(3-chlorophenyl)-3-(3-methoxypropoxy)propyl(isopropyl)carbamate

HRID 426047Notes

Reaction equation

HRID 426047 reaction equation
C(N)(C)C.[BH4-].[Na+].[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]([OH:28])[CH2:15][CH2:16][N:17]([CH:25]([CH3:27])[CH3:26])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=[CH:12][CH:13]=1.[H-].[Na+].CS(O[CH2:36][CH2:37][CH2:38][O:39][CH3:40])(=O)=O>C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]([O:28][CH2:36][CH2:37][CH2:38][O:39][CH3:40])[CH2:15][CH2:16][N:17]([CH:25]([CH3:26])[CH3:27])[C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:23])[CH3:21])[CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 5

HCID 6363IsopropylamineHCID 24758Sodium hydrideHCID 4311764Sodium borohydrideHCID 116939633-Methoxypropyl methanesulfonateHCID 59364370Tert-butyl 3-(3-chlorophenyl)-3-hydroxypropyl(isopropyl)carbamate

Product 1

HCID 66704397Tert-butyl 3-(3-chlorophenyl)-3-(3-methoxypropoxy)propyl(isopropyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-butyl 3-(3-chlorophenyl)-3-hydroxypropyl(isopropyl)carbamate was obtained using procedures analogous to Preparation A, Steps 1-6, using isopropylamine in Step 1 and NaBH4 in Step 6. To a 0° C. solution of tert-butyl 3-(3-chlorophenyl)-3-hydroxypropyl(isopropyl)carbamate (158 mg, 0.48 mmol) in THF (5 mL) was added NaH (60 mg, 1.45 mmol) and the reaction was allowed to stir for 5 minutes. 3-methoxypropyl methanesulfonate (810 mg, 4.8 mmol) was then added and the reaction was heated to reflux for 2.5 hrs. After cooling to room temperature, the reaction was quenched with saturated ammonium chloride solution at 0° C. The aqueous layer was extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, filtered, evaporated and purified via ISCO to afford tert-butyl 3-(3-chlorophenyl)-3-(3-methoxypropoxy)propyl(isopropyl)carbamate. MS ESI+ve m/z 422 (M+Na).

Workup

  1. customanalogous to Preparation A, Steps 1-6
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 2.5 hrs
  4. customthe reaction was quenched with saturated ammonium chloride solution at 0° C
  5. extractionThe aqueous layer was extracted with EtOAc (2×)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. custompurified via ISCO

Sources & evidence

ORD record
ord-0f48f4bf0a2e4170b8ed97fcb960e3b0
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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