HCID 70403914, compound → HCID 70403452, compound

HRID 2231367Notes

Reaction equation

HRID 2231367 reaction equation
C([O:4][C@H:5]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=O)C>CO.N.C1(C)C=CC=CC=1.C(OCC)(=O)C>[OH:4][C@H:5]([CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

Participants

5

Reactant 1

HCID 70403914HCID 70403914, compound

Product 1

HCID 70403452HCID 70403452, compoundYield 86.2%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 887MethanolSolventHCID 21584019Toluene ethylacetateSolvent

Procedure

8.0 g of tert.butyl 2(R)-acetoxy-4-(4-nitrophenyl)butanoate were dissolved in 200 ml of methanol saturated with ammonia at 0° C. and the mixture was stirred for 16 hours. Evaporation of the mixture in vacuo gave 7 g of an almost colorless oil which was dissolved in an equal volume of diethyl ether/n-hexane (1;1) and eluted through a silica gel column with the same solvent mixture to give 6 g of tert.butyl 2(R)-hydroxy-4-(4-nitrophenyl)butanoate as a colorless crystalline solid having a melting point of 41°-42° C.

Workup

  1. customEvaporation of the mixture in vacuo
  2. customgave 7 g of an almost colorless oil which
  3. washeluted through a silica gel column with the same solvent mixture

Sources & evidence

ORD record
ord-1bad1c9971b34e9ab9e35ebf50bade43
Source dataset
uspto-grants-1988_11
Patent number
US04782149

Reaction notes

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