Aluminum isopropoxide → Methyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

HRID 259914Notes

Reaction equation

HRID 259914 reaction equation
[CH2:1]([C@H:8]([NH:13][C:14](=[O:17])[O:15][CH3:16])[C:9](=[O:12])[CH2:10][Cl:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-]>C(O)(C)C>[CH2:1]([C@H:8]([NH:13][C:14](=[O:17])[O:15][CH3:16])[C@H:9]([OH:12])[CH2:10][Cl:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11143Aluminum isopropoxideHCID 9881533methyl (S)-(1-benzyl-3-chloro-2-oxo-propyl)carbamate

Product 1

HCID 10945089Methyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamateYield 89.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

25.57 g of methyl (S)-(1-benzyl-3-chloro-2-oxo-propyl)carbamate were added portionwise at 22° C. to a suspension of 21.44 g of aluminum isopropoxide in 260 ml of isopropanol. The suspension was stirred at 50° C./400 mbar for 2 hours, hydrolyzed at 0° C. with 100 ml of 3N hydrochloric acid, subsequently concentrated to a volume of 125 ml, diluted with 125 ml of water, cooled to 0° C. and filtered. The residue was washed with water/isopropanol (4:1) and dried, yielding 23.01 g (89%) of isomerically-pure methyl (1S,2S)-(1-benzyl-3-chloro-2-hydroxypropyl)-carbamate, m.p. 162°-163.5° C. IR (KBr): 3323s, br. (NH, OH), 1689 (C=O), 1546s (amide II).

Workup

  1. concentrationhydrolyzed at 0° C. with 100 ml of 3N hydrochloric acid, subsequently concentrated to a volume of 125 ml
  2. additiondiluted with 125 ml of water
  3. temperaturecooled to 0° C.
  4. filtrationfiltered
  5. washThe residue was washed with water/isopropanol (4:1)
  6. customdried

Sources & evidence

ORD record
ord-421ce13baecb433fb6b38d6c29a3938e
Source dataset
uspto-grants-1996_06
Patent number
US05523463

Reaction notes

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