Methanol → HCID 178484021, compound

HRID 967136Notes

Reaction equation

HRID 967136 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][CH2:18][C:19](O)=[O:20])[CH2:13][CH2:12]1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO>O1CCCC1>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][CH2:18][CH2:19][OH:20])[CH2:13][CH2:12]1)[CH3:9])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 887MethanolHCID 178484023HCID 178484023, compound

Product 1

HCID 178484021HCID 178484021, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

0.898 g (3.0 mmol) of trans-3-{4-[(tert-butoxycarbonyl-methyl-amino)-methyl]-cyclohexyl}-propionic acid dissolved in 10.0 ml of tetrahydrofuran were added slowly and at 0° C. to 4.5 ml of an 1M solution of boran-tetrahydrofuran-complex in tetrahydrofuran. The reaction mixture was then stirred at room temperature for 1 hour. Subsequently, 10 ml of methanol were added and the reaction mixture evaporated. It was then poured into 50 ml of an ice/water/aqueous sodium hydrogen carbonate mixture and extracted 3 times with 50 ml of dichloromethane. The combined dichloromethane phases were dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 4:1 v/v mixture of dichloromethane and ether as the eluent giving 0.690 g (80.6%) trans-[4-(3-hydroxy-propyl)-cyclohexylmethyl]-methyl-carbamic acid tert-butyl ester as colorless viscous oil, MS: 286 (MH+).

Workup

  1. customthe reaction mixture evaporated
  2. additionIt was then poured into 50 ml of an ice/water/aqueous sodium hydrogen carbonate mixture
  3. extractionextracted 3 times with 50 ml of dichloromethane
  4. dry with materialThe combined dichloromethane phases were dried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue formed
  7. customwas chromatographed on silica gel with a 4:1 v/v mixture of dichloromethane and ether as the eluent

Sources & evidence

ORD record
ord-d433421d99714b64abb079242c4f46b6
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

Loading…