Potassium bisulfate → Boc-cyclohexylglycinal

HRID 256816Notes

Reaction equation

HRID 256816 reaction equation
[C:1]([N:8]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:9][C:10](O)=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].OS([O-])(=O)=O.[K+]>CCOCC.O>[C:1]([N:8]([CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)[CH2:9][CH:10]=[O:11])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 516920Potassium bisulfateHCID 10563100n-Boc-n-cyclohexylglycineHCID 21226445Aluminium lithium hydride

Product 1

HCID 19784133Boc-cyclohexylglycinal

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 40 g (0.119 mole) of BOC-CYCLOHEXYLGLYCINE, O,N-DIMETHYLHYDROXAMIDE in 550 ml Et2O was cooled in ice and 148 ml (0.148 mole) of a 1M solution of LiAlH4 in Et2O added over 0.5 hour. After an additional 15 minutes, the mixture was treated cautiously with 28 g of KHSO4 in 100 ml H2O. The mixture was filtered through Celite and washed with 10% citric acid and saturated NaHCO3. After drying the solvent was removed under reduced pressure to give the crude BOC-CYCLOHEXYLGLYCINAL. The material was used immediately in the following reaction. ##STR175##

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with 10% citric acid and saturated NaHCO3
  3. customAfter drying the solvent
  4. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-83e78408960341df9e98dbcf9734e612
Source dataset
uspto-grants-1993_11
Patent number
US05260278

Reaction notes

Loading…